(R)-1-[4-[3-(acetyloxy)-1-pyrrolidinyl]-2-butynyl]-2-pyrrolidinone → (S)-1-[4-[3-(Acetyloxy)-1-pyrrolidinyl]-2-butynyl]-2-pyrrolidinone

HRID 1534549Notes

Reaction equation

HRID 1534549 reaction equation
[C:1]([O:4][C@H:5]1[CH2:9][CH2:8][N:7]([CH2:10][C:11]#[C:12][CH2:13][N:14]2[CH2:18][CH2:17][CH2:16][C:15]2=[O:19])[CH2:6]1)(=[O:3])[CH3:2].C([O:23][C@@H:24]1[CH2:28][CH2:27][N:26]([CH2:29][C:30]#[C:31][CH2:32][N:33]2[CH2:37][CH2:36][CH2:35][C:34]2=[O:38])[CH2:25]1)(=O)C>>[C:1]([O:4][C@H:5]1[CH2:9][CH2:8][N:7]([CH2:10][C:11]#[C:12][CH2:13][N:14]2[CH2:18][CH2:17][CH2:16][C:15]2=[O:19])[CH2:6]1)(=[O:3])[CH3:2].[OH:3][C@@H:35]1[CH2:36][CH2:37][N:33]([CH2:32][C:31]#[C:30][CH2:29][N:26]2[CH2:27][CH2:28][CH2:24][CH2:25]2)[C:34]1=[O:38].[OH:23][CH:24]1[CH2:28][CH2:27][N:26]([CH2:29][C:30]#[C:31][CH2:32][N:33]2[CH2:37][CH2:36][CH2:35][C:34]2=[O:38])[CH2:25]1

Participants

5

Reactant 2

HCID 15046673(R)-1-[4-[3-(acetyloxy)-1-pyrrolidinyl]-2-butynyl]-2-pyrrolidinoneHCID 15046674(S)-1-[4-[3-(Acetyloxy)-1-pyrrolidinyl]-2-butynyl]-2-pyrrolidinone

Product 3

HCID 15046674(S)-1-[4-[3-(Acetyloxy)-1-pyrrolidinyl]-2-butynyl]-2-pyrrolidinoneHCID 15046676(R)-3-Hydroxy-1-[4-(1-pyrrolidinyl)-2-butynyl]-2-pyrrolidinoneHCID 15046679(Racemic)-1-[4-(3-Hydroxy-1-pyrrolidinyl)-2-butynyl]-2-pyrrolidinone

Procedure

Following the procedure of Example 46, the (S) or (R) isomers of the desired product were prepared from (S) or (R)-1-[4-[3-(acetyloxy)-1-pyrrolidinyl]-2-butynyl]-2-pyrrolidinone.

Sources & evidence

ORD record
ord-5d34bfc1afb3444f9dc616e4721c2e8a
Source dataset
uspto-grants-1992_02
Patent number
US05089518

Reaction notes

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