Propargyl alcohol → N-Desethyloxybutynin, (S)-

HRID 370365Notes

Reaction equation

HRID 370365 reaction equation
C1(C(C2C=CC=CC=2)(O)C(O)=O)CCCCC1.[CH3:18][CH2:19][N:20]([CH2:23][C:24]#[C:25][CH2:26][O:27][C:28]([C@:30]([OH:43])([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[CH:31]1[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1)=[O:29])CC.C(OC(Cl)=O)C(C)C.C(O)C#C.C(N(C(C)C#CO)CC1C=CC(OC)=CC=1)C.C1(C(C2CCCCC2)(O)C(OC#CCCN(CC)CC2C=CC(OC)=CC=2)=O)C=CC=CC=1.C(Cl)(=O)OC(Cl)C>>[C:31]1([C@:30]([CH:37]2[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42]2)([OH:43])[C:28]([O:27][CH2:26][C:25]#[C:24][CH2:23][NH:20][CH2:19][CH3:18])=[O:29])[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

8

Reactant 7

HCID 7859Propargyl alcoholHCID 62365Isobutyl chloroformateHCID 97700(+-)-Cyclohexylphenylglycolic acidHCID 5213051-Chloroethyl chloroformateHCID 6098167AroxybutyninHCID 54413069N-ethyl-N-(4-methoxybenzyl)aminobutynyl phenylcyclohexyl-glycolateHCID 69648212N-ethyl-N-(4-methoxybenzyl)aminobutynol

Product 1

HCID 9945371N-Desethyloxybutynin, (S)-

Procedure

The method according to claim 1, wherein said single enantiomer of cyclohexylphenyl glycolic acid is the (S) enantiomer, said alkyl chloroformate is isobutylchloroformate, said sidechain propargyl alcohol derivative of formula (III) is N-ethyl-N-(4-methoxybenzyl)aminobutynol, and said single enantiomer of structure (II) is N-ethyl-N-(4-methoxybenzyl)aminobutynyl phenylcyclohexyl-glycolate, which is treated with α-chloroethyl carbonochloridate to provide (S)-4-ethylamino-2-butynyl phenylcyclohexylglycolate.

Sources & evidence

ORD record
ord-11bf3b40865d45ab89832788d86873e8
Source dataset
uspto-grants-2000_10
Patent number
US06140529

Reaction notes

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