Methyl cyclopentylmandelate → HCID 66959229, compound

HRID 1366720Notes

Reaction equation

HRID 1366720 reaction equation
[CH3:1][O:2][C:3](=[O:17])[C:4]([CH:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1)([OH:11])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.O[C@@H:19]1[CH:24]2C[CH2:26][N:21]([CH2:22][CH2:23]2)[CH2:20]1>C1(C)C=CC=CC=1>[N:21]12[CH2:22][CH2:23][CH:24]([CH2:19][CH2:20]1)[C@@H:1]([O:2][C:3](=[O:17])[C:4]([CH:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1)([OH:11])[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)[CH2:26]2

Participants

4

Reactant 2

HCID 89233Methyl cyclopentylmandelateHCID 914043-Quinuclidinol, (-)-

Product 1

HCID 66959229HCID 66959229, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Prepared using the same method as for Intermediate I-1, but from 13.5 g (0.0576 mol) of 2-Cyclopentyl-2-hydroxy-2-phenylacetic acid methyl ester (commercially available) dissolved in 350 ml of toluene, 8.0 g (0.063 mol) of (3R)-3-hydroxy-1-azabicyclo[2.2.2]octane and 0.91 g (0.023 mol) of HNa (60% dispersion in mineral oil). The yield was 13.1 g (69%) of the title product as an oil mixture of diastereomers, structure confirmed by 1H-NMR; The two diastereomers I-5a and I-5b were separated after several crystallizations.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-7c48398faccc40f4b3e2f1c324b355ef
Source dataset
uspto-grants-2011_02
Patent number
US07893087B2

Reaction notes

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