(S)-(+)-2-Methylpiperidine → 4-[(2S)-2-methylpiperidin-1-yl]-3-(trifluoromethyl)benzoic acid

HRID 2410493Notes

Reaction equation

HRID 2410493 reaction equation
[CH3:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][N:3]1[C:8]1[CH:16]=[CH:15][C:11]([C:12]([OH:14])=[O:13])=[CH:10][C:9]=1[C:17]([F:20])([F:19])[F:18].C[C@H]1CCCCN1>>[CH3:1][C@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][N:3]1[C:8]1[CH:16]=[CH:15][C:11]([C:12]([OH:14])=[O:13])=[CH:10][C:9]=1[C:17]([F:19])([F:18])[F:20]

Participants

3

Reactant 2

HCID 6427443(S)-(+)-2-MethylpiperidineHCID 580662284-[(2R)-2-methylpiperidin-1-yl]-3-(trifluoromethyl)benzoic acid

Product 1

HCID 580662204-[(2S)-2-methylpiperidin-1-yl]-3-(trifluoromethyl)benzoic acid

Procedure

The title compound was prepared following the procedure described in Intermediate 10 Steps 1 and 2, but starting from (S)-(+)-2-methylpiperidine. It was isolated as a beige powder. 1H NMR (DMSO-d6) δ 13.29 (s, 1H), 8.23-8.12 (m, 2H), 7.68 (d, J=8.4 Hz, 1H), 3.07 (m, 1H), 2.94-2.81 (m, 1H), 2.61-2.45 (m, 2H), 1.75 (m, 1H), 1.67-1.18 (m, 4H), 0.71 (d, J=6.1 Hz, 3H). HPLC (Method A), Rt 4.79 min (Purity: 99.9%). LC/MS (Method B): 286.2 (M−H)−, 288.0 (M+H)+.

Workup

  1. customIt was isolated as a beige powder

Sources & evidence

ORD record
ord-23851179dbc9401a8cadbaacbfde6ca7
Source dataset
uspto-grants-2014_08
Patent number
US08815919B2

Reaction notes

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