(S)-Piperidin-3-ylmethanol hydrochloride → ((R)-3-Hydroxymethyl-piperidin-1-yl)-[5-(4-methyl-5-trifluoromethyl-isoxazol-3-yl)-thiophen-2-yl]-methanone

HRID 572316Notes

Reaction equation

HRID 572316 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[O:7][N:6]=[C:5]([C:8]2[S:12][C:11]([C:13](Cl)=[O:14])=[CH:10][CH:9]=2)[C:4]=1[CH3:16].Cl.[NH:20]1[CH2:25][CH2:24][CH2:23][C@H:22]([CH2:26][OH:27])[CH2:21]1>>[OH:27][CH2:26][C@@H:22]1[CH2:23][CH2:24][CH2:25][N:20]([C:13]([C:11]2[S:12][C:8]([C:5]3[C:4]([CH3:16])=[C:3]([C:2]([F:18])([F:17])[F:1])[O:7][N:6]=3)=[CH:9][CH:10]=2)=[O:14])[CH2:21]1

Participants

3

Reactant 2

HCID 70700777(S)-Piperidin-3-ylmethanol hydrochlorideHCID 866283515-(4-Methyl-5-trifluoromethyl-isoxazol-3-yl)-thiophene-2-carbonyl chloride

Product 1

HCID 25212015((R)-3-Hydroxymethyl-piperidin-1-yl)-[5-(4-methyl-5-trifluoromethyl-isoxazol-3-yl)-thiophen-2-yl]-methanone

Procedure

Prepared from 5-(5-Trifluoromethyl-4-methyl-isoxazol-3-yl)-thiophene-2-carbonyl chloride (74 mg, 0.25 mmol, as prepared in Example 2 Method B) and (S)-1-piperidin-3-yl-methanol, hydrochloride (76 mg, 0.5 mmol) in the same manner as the S isomer (Example 69). Gummy solid (56 mg, 60%). LC/MS 5.86 min, [M+1]+ 375.

Workup

  1. customLC/MS 5.86 min, [M+1]+ 375

Sources & evidence

ORD record
ord-6ae0bb8bd61f4c17863f4e57ebf9e777
Source dataset
uspto-grants-2015_05
Patent number
US09029397B2

Reaction notes

Loading…