(s)-1-(5-Methoxy-2,3-dihydro-benzofuran-2-ylmethyl)-4-(4-chloro-benzyl)-piperidin-4-ol → (S)-1-(5-Hydroxy-2,3-dihydro-benzofuran-2-ylmethyl)-4-(4-chloro-benzyl)-piperidin-4-ol

HRID 278410Notes

Reaction equation

HRID 278410 reaction equation
C[O:2][C:3]1[CH:4]=[CH:5][C:6]2[O:10][C@H:9]([CH2:11][N:12]3[CH2:17][CH2:16][C:15]([CH2:19][C:20]4[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=4)([OH:18])[CH2:14][CH2:13]3)[CH2:8][C:7]=2[CH:27]=1>CN(C=O)C>[OH:2][C:3]1[CH:4]=[CH:5][C:6]2[O:10][C@H:9]([CH2:11][N:12]3[CH2:17][CH2:16][C:15]([CH2:19][C:20]4[CH:21]=[CH:22][C:23]([Cl:26])=[CH:24][CH:25]=4)([OH:18])[CH2:14][CH2:13]3)[CH2:8][C:7]=2[CH:27]=1

Participants

3

Reactant 1

HCID 54036117(s)-1-(5-Methoxy-2,3-dihydro-benzofuran-2-ylmethyl)-4-(4-chloro-benzyl)-piperidin-4-ol

Product 1

HCID 54190367(S)-1-(5-Hydroxy-2,3-dihydro-benzofuran-2-ylmethyl)-4-(4-chloro-benzyl)-piperidin-4-ol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound, MS: m/e=374.2 (M+H+) [α]=+32.4° (c=1.0, DMF), >99% e.e. by chiral phase HPLC, was prepared from (S)-1-(5-methoxy-2,3-dihydro-benzofuran-2-ylmethyl)-4-(4-chloro-benzyl)-piperidin-4-ol.

Sources & evidence

ORD record
ord-e1680135a36e4bf090430466283af315
Source dataset
uspto-grants-2002_03
Patent number
US06359138B1

Reaction notes

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