2-Chloro-5-methyl-1,3-benzoxazole → benzyl(2S)-1-(5-methyl-1,3-benzoxazol-2-yl)-2-piperidinecarboxylate

HRID 2298848Notes

Reaction equation

HRID 2298848 reaction equation
Cl[C:2]1[O:3][C:4]2[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][C:5]=2[N:6]=1.[Cl-].[CH2:13]([O:20][C:21]([C@@H:23]1[CH2:28][CH2:27][CH2:26][CH2:25][NH2+:24]1)=[O:22])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>>[CH3:11][C:8]1[CH:9]=[CH:10][C:4]2[O:3][C:2]([N:24]3[CH2:25][CH2:26][CH2:27][CH2:28][C@H:23]3[C:21]([O:20][CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[O:22])=[N:6][C:5]=2[CH:7]=1

Participants

3

Reactant 2

HCID 99896072-Chloro-5-methyl-1,3-benzoxazoleHCID 86591486(2S)-2-((benzyloxy)carbonyl]piperidinium chloride

Product 1

HCID 54429299benzyl(2S)-1-(5-methyl-1,3-benzoxazol-2-yl)-2-piperidinecarboxylate

Procedure

The title compound was prepared by a similar method to Preparation 2 from 2-chloro-5-methyl-1,3-benzoxazole [see J.Med.Chem, 1988, 31, 1719-1728] and (2S)-2-[(benzyloxy)carbonyl]piperidinium chloride [see EP 530167 A1 930303]. The crude product was purified by column chromatography on silica gel eluting with a solvent gradient of 90:10 changing to 70:30, by volume, hexane:ethyl acetate to afford benzyl(2S)-1-(5-methyl-1,3-benzoxazol-2-yl)-2-piperidinecarboxylate as an oil.

Workup

  1. customThe crude product was purified by column chromatography on silica gel eluting with a solvent gradient of 90:10 changing to 70:30, by volume, hexane

Sources & evidence

ORD record
ord-ec6960026f3f4033952346d91362fead
Source dataset
uspto-grants-2002_12
Patent number
US06495549B1

Reaction notes

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