2-Chloro-5,6-dimethyl-1,3-benzoxazole → benzyl (2S)-1-[5,6-dimethyl-1,3-benzoxazol-2-yl]-2-piperidinecarboxylate

HRID 1276184Notes

Reaction equation

HRID 1276184 reaction equation
Cl[C:2]1[O:3][C:4]2[CH:10]=[C:9]([CH3:11])[C:8]([CH3:12])=[CH:7][C:5]=2[N:6]=1.[Cl-].[CH2:14]([O:21][C:22]([C@@H:24]1[CH2:29][CH2:28][CH2:27][CH2:26][NH2+:25]1)=[O:23])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>>[CH3:12][C:8]1[C:9]([CH3:11])=[CH:10][C:4]2[O:3][C:2]([N:25]3[CH2:26][CH2:27][CH2:28][CH2:29][C@H:24]3[C:22]([O:21][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[O:23])=[N:6][C:5]=2[CH:7]=1

Participants

3

Reactant 2

HCID 140741872-Chloro-5,6-dimethyl-1,3-benzoxazoleHCID 86591486(2S)-2-((benzyloxy)carbonyl]piperidinium chloride

Product 1

HCID 54542247benzyl (2S)-1-[5,6-dimethyl-1,3-benzoxazol-2-yl]-2-piperidinecarboxylate

Procedure

The title compound was prepared by a similar method to Preparation 2 from 2-chloro-5,6-dimethyl-1,3-benzoxazole [see J. Med. Chem. (1972), 15, 523-9] and (2S)-2-[(benzyloxy)carbonyl]piperidine [see EP 530167 A1 930303]. The crude product was purified by column chromatography on silica gel eluting with a solvent gradient of 100:0 changing to 80:20, by volume, hexane:ethyl acetate to afford benzyl (2S)-1-[5,6-dimethyl-1,3-benzoxazol-2-yl]-2-piperidinecarboxylate as a yellow coloured solid.

Workup

  1. customThe crude product was purified by column chromatography on silica gel eluting with a solvent gradient of 100:0 changing to 80:20, by volume, hexane

Sources & evidence

ORD record
ord-bbbb229784454d519f74e92237adb867
Source dataset
uspto-grants-2000_12
Patent number
US06166011

Reaction notes

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