HCID 7195215, compound → 2,alpha-Dichlorophenyl acetic acid-(R)-2-(1-pyrrolidinyl)-1-phenylethyl ester

HRID 1786723Notes

Reaction equation

HRID 1786723 reaction equation
[C:1]1([C@@H:7]([OH:14])[CH2:8][N:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[CH:22]([Cl:26])[C:23](Cl)=[O:24]>O1CCCC1.CN(C1C=CN=CC=1)C>[N:9]1([CH2:8][C@H:7]([O:14][C:23](=[O:24])[CH:22]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[Cl:15])[Cl:26])[C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

5

Reactant 2

HCID 7195215HCID 7195215, compoundHCID 575981452,alpha-Dichlorophenyl acetyl chloride

Product 1

HCID 866151242,alpha-Dichlorophenyl acetic acid-(R)-2-(1-pyrrolidinyl)-1-phenylethyl ester

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 5.7 g of (R)-1-phenyl-2-(1-pyrrolidinyl)-ethanol in 25 ml of tetrahydrofurane was added to a solution of 6.5 g of 2,α-dichlorophenyl acetyl chloride in 25 ml of tetrahydrofurane containing 0.9 g of 4-dimethylamine pyridine. According to a similar procedure as in example 3, a mixture of diastereomeric esters containing 72% (R,R) and 28% (R,S) of the product in a yield of 8.4 g (74%) was obtained.

Workup

  1. customwas obtained

Sources & evidence

ORD record
ord-86cc9ea167154d3690d3c13678780072
Source dataset
uspto-grants-2009_03
Patent number
US07507827B2

Reaction notes

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