1-Methyl-3-pyrrolidinol, (+)- → 2-Hydroxy-2,2-dithien-2-ylacetic acid (3S)-1-methylpyrrolidin-3-yl ester

HRID 458891Notes

Reaction equation

HRID 458891 reaction equation
[CH3:1][O:2][C:3](=[O:16])[C:4]([OH:15])([C:10]1[S:11][CH:12]=[CH:13][CH:14]=1)[C:5]1[S:6][CH:7]=[CH:8][CH:9]=1.[CH3:17][N:18]1[CH2:22]C[C@H:20](O)[CH2:19]1>C1(C)C=CC=CC=1>[CH3:17][N:18]1[CH2:19][CH2:20][C@H:1]([O:2][C:3](=[O:16])[C:4]([OH:15])([C:5]2[S:6][CH:7]=[CH:8][CH:9]=2)[C:10]2[S:11][CH:12]=[CH:13][CH:14]=2)[CH2:22]1

Participants

4

Reactant 2

HCID 6435041-Methyl-3-pyrrolidinol, (+)-HCID 11414137Methyl alpha-hydroxy-alpha-2-thienyl-2-thiopheneacetate

Product 1

HCID 866022572-Hydroxy-2,2-dithien-2-ylacetic acid (3S)-1-methylpyrrolidin-3-yl esterYield 25%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Prepared as described in Intermediate I-5 from 0.98 g (0.00385 mol) of 2-Hydroxy-2,2-dithien-2-ylacetic acid methyl ester in 30 ml of toluene, 0.39 g (0.00385 mol) of (3S)-1-methylpyrrolidin-3-ol (Intermediate I-20) and 0.108 g (0.0027 mol) of HNa (60% dispersion in mineral oil). The yield was 0.31 g (25%) of the title product.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-fbcc2385c6c54bd69da4a10e3120f3cc
Source dataset
uspto-grants-2007_03
Patent number
US07192978B2

Reaction notes

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