alpha-Methoxy-alpha-(trifluoromethyl)phenylacetyl chloride, (S)-(+)- → (R)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionic acid (cis)-1-benzyl-4-(4-methyl-benzyl)-piperidin-3-yl ester

HRID 382787Notes

Reaction equation

HRID 382787 reaction equation
[CH3:1][C:2]1[CH:15]=[CH:14][C:5]([CH2:6][CH:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH:8]2[OH:13])=[CH:4][CH:3]=1.[CH3:16][O:17][C@@:18]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)([C:22]([F:25])([F:24])[F:23])[C:19](Cl)=[O:20]>>[CH2:1]([N:10]1[CH2:11][CH2:12][C@H:7]([CH2:6][C:5]2[CH:4]=[CH:3][C:2]([CH3:1])=[CH:15][CH:14]=2)[C@H:8]([O:13][C:19](=[O:20])[C@:18]([O:17][CH3:16])([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:22]([F:25])([F:24])[F:23])[CH2:9]1)[C:2]1[CH:15]=[CH:14][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 2724611alpha-Methoxy-alpha-(trifluoromethyl)phenylacetyl chloride, (S)-(+)-HCID 18362020(3SR,4SR)-4-(4-methyl-benzyl)-piperidin-3-ol

Product 1

HCID 59972010(R)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionic acid (cis)-1-benzyl-4-(4-methyl-benzyl)-piperidin-3-yl esterYield 33%

Procedure

The title compound was prepared from (3SR,4SR)-4-(4-methyl-benzyl)-piperidin-3-ol and (S)-(+)-alpha-methoxy-alpha-trifluoromethylphenylacetyl chloride in 33% yield as a yellow oil.

Sources & evidence

ORD record
ord-ef152f3540604c79b311e3691a9df0a7
Source dataset
uspto-grants-2001_10
Patent number
US06310213B1

Reaction notes

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