Rectify's molecular poetry thread

[Rectify]

Whichever one I took today doesn't feel that toxic.

 

[Rectify]

EVEN_BETTER
1-(1,3-dioxoindan-5-yl)-2-methylamino-1-carbomethoxypropane

 

[Rectify]

BRAD_PITT
1-(1,3-dioxoindan-5-yl)-2-(1-pyrrolidinyl)-1-oxopropane

JOHNNY_DEPP
1-(2-oxoindan-5-yl)-2-(1-pyrrolidinyl)-1-oxopropane

New Car Smell.

 

[Rectify]

benzene

Cl-(C=O)-CH2-(C=O)-Cl

1,3-dichloroacyl-maleic acid

AlCl3(s)

1,3-dioxoindan

Protect oxo's with ethylene glycol, then react with Cl-(C=O)CH2CH3 and AlCl3. Then Br2, then deprotect with H+.

1-(1,3-dioxoindan-5-yl)-1-oxo-2-bromopropane

pyrrolidine

1-(1,3-dioxo-indan-5-yl)-1-oxo-2-(1-pyrrolidinyl)-propane

You might have to fiddle around with the protecting groups, but this is the gist of it.

 

[Rectify]

GEETERED
1-(indole-3-yl)-1-carbomethoxy-2-aminopropane

SKEETERED
1-(indole-3-yl)-1-carbomethoxy-2-dimethylaminoethane

 

[Rectify]

acetylene

Diels Alder

benzene

1-chloro-1-oxopropane

AlCl3

Friedel Crafts

1-phenyl-1-oxopropane

Br2

1-phenyl-2-bromo-1-oxopropane

CH3CH2NH2

1-phenyl-1-oxo-2-ethylaminopropane

NaBH4

1-phenyl-1-hydroxy-2-ethylaminopropane

Cl-(C=O)-Cl

1-phenyl-1-chloro-2-ethylaminopropane

KCN

1-phenyl-1-cyano-2-ethylaminopropane

H3O+

1-phenyl-1-carboxy-2-ethylaminopropane

FANCY_FEAST
1-phenyl-1-carbomethoxy-2-ethylaminopropane

Bon apetit!

 

[Rectify]

BILLY
1-(4-methylphenyl)-1-carbomethoxy-2-ethylaminopropane

Same as above, except for toluene instead of benzene.

 

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CIRRUS
1-(3,4,5-trimethoxyphenyl)-1-carbomethoxy-2-aminopropane

 

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SIRIUSLY
1-(3,5-dimethoxy-4-pentylphenyl)-1-carbomethoxy-2-aminopropane

 

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BRO_MO
1-(3,5-dimethoxy-4-bromophenyl)-1-carbomethoxy-2-aminopropane

 

[Rectify]

It Has Been Said That A Critic Knows

LACOSTE
3-amino-4-phenyl-tetrahydrofuran

Of Everything And The

GREAT_VALUE
5-oxo-3-amino-4-phenyl-tetrahydrofuran

Of Nothing.

 

[Rectify]

SMACKED_OUT
5-oxo-3-methylamino-4-(4-methoxyphenyl)-tetrahydrofuran

 

[Rectify]

ALCOHOLIC_AMPHETAMINE
N-(2-hydroxyethyl)-1-phenyl-2-aminopropane

Probably weak. I don't know.

 

[unodelacosa]

DOUBLE_DEXTER_FINN_AGAIN

(1S,2S)-1-phenyl-1-carbomethoxy-2-methylaminopropane

from

(1R,2S)-1-phenyl-1-hydroxy-2-methylaminopropane

Ah yes, my good ol' buddy of the Mà Huàng persuasion.

Actually, I think the hydroxyl group may switch around the stereochemistry of the one spot after it undergoes a substitution reaction.

Yes, starting from the (1R,2S)-configuration, the hydroxyl group is converted to a leaving group, such as a mesylate or tosylate. But it's switched back during the second substitution that reacts the resulting compound from the first step with… well I guess something like, α-methoxyacetyl chloride, introducing the carbomethoxy group, no? I'm speculating on the synthetic route a bit here.

Anyway, if that is the case, then this is the correct precursor:

(1S,2S)-1-phenyl-1-hydroxy-2-methylaminopropane

Pseudoefffffffiiiiii mean pseudomàhuàng, IIRC. Hmm, I'm reminded of PPA and Aminorex synthesis at the moment.

BUT it undergoes 2 substitution reactions, so the former would be correct.

Right? That's how I see it, too. One would start from the (1R,2S) config, and not the pseudo one, (1S,2S).

Errg, Forget Stereochemistry! All I Know Is That Ephedrine Comes In 4 Stereochemicals, And One Of Them Is Correct. Specifically, It Has A (2S).

Forgive me for being pedantic and splitting hairs a bit here… The pair of enantiomers with the stereochemistry (1R,2S) and (1S,2R) is traditionally designated "ephedrine", while the pair of enantiomers with the stereochemistry (1R,2R) and (1S,2S) is called "pseudoephedrine". I know you know this already, but I figured it would hurt to post as a reminder to anyone reading this thread… who probs know it too, but … it's in the interests of science and, by extension perhaps if not directly, harm reduction.

 

[unodelacosa]

ALCOHOLIC_AMPHETAMINE
N-(2-hydroxyethyl)-1-phenyl-2-aminopropane

Probably weak. I don't know.

Probably weak as a stimulant, you're saying, right? And yeah I can't imagine that n-substituted ethylhydroxy bond would do much to help w/potency or even perceptible activity without super high/dangerous doses.

 

[Rectify]

I always thought it depended on whether the ephedrine came from ma huang or which brand of cold pills that were used.

I know there are 2^n where n = 2 chiral centers means that there are 4 possible stereoisomers of ephedrine.

Interestingly, I have found that methamphetamine made from ma huang extract is smoother and weaker than that made from cold pills. I don't know why.

But believe it or not, I am not a meth chef.

 

[Rectify]

BOB_DOBBS - The Church Of The SubGenius
1-(4-bromo-2,5-dimethoxyphenyl)-1-carbomethoxy-2-aminopropane

 

[Rectify]

Sometimes you feel like a

FINNOXIDE
1-phenyl-1-carbophenoxy-2-methylaminopropane

 

[Rectify]

JASON_CHRISTOPHER
methyl 20(1R,2R,3S,5S)-3-(phenoxy)-8-methyl-8-azabicyclp[3.2.1]octane-2-carboxylate

HO-CH2CH2-O-CH2CH2-OH

JAMES
Stronger Than It Looks

 

[Rectify]

JASON_CHRISTOPHER
methyl (1R,2R,3S,5S)-3-(phenoxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate

If I Knew How To Make It, I Would Tell You So.

HO-CH2CH2-O-CH2CH2-OH

JAMES
Stronger Than It Looks

HUFFABLE_ALLICIN_WUNDERLANDE.
diallylsulfur