2,5-Dichlorobenzooxazole → benzyl(2S)-1-(5-chloro-1,3-benzoxazol-2-yl)-2-piperidinecarboxylate

HRID 2119399Notes

Reaction equation

HRID 2119399 reaction equation
[Cl-].[CH2:2]([O:9][C:10]([C@@H:12]1[CH2:17][CH2:16][CH2:15][CH2:14][NH2+:13]1)=[O:11])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl[C:19]1[O:20][C:21]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][C:22]=2[N:23]=1>>[Cl:28][C:25]1[CH:26]=[CH:27][C:21]2[O:20][C:19]([N:13]3[CH2:14][CH2:15][CH2:16][CH2:17][C@H:12]3[C:10]([O:9][CH2:2][C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=3)=[O:11])=[N:23][C:22]=2[CH:24]=1

Participants

3

Reactant 2

HCID 103975782,5-DichlorobenzooxazoleHCID 86591486(2S)-2-((benzyloxy)carbonyl]piperidinium chloride

Product 1

HCID 53932308benzyl(2S)-1-(5-chloro-1,3-benzoxazol-2-yl)-2-piperidinecarboxylate

Procedure

The title compound was prepared by a similar method to Preparation 2 from (2S)-2-[(benzyloxy)carbonyl]piperidinium chloride [see EP 530167 A1 930303] and 2,5-dichloro-1,3-benzoxazole [see J.O.C. (1996), 61(10), 3289-3297]. The crude product was purified by column chromatography on silica gel eluting with a solvent system of 95:5, by volume, hexane:ethyl acetate to afford benzyl (2S)-1-(5-chloro-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 system of 95:5, by volume, hexane

Sources & evidence

ORD record
ord-37a51b6a33434ad8aafa3676e7dfb32a
Source dataset
uspto-grants-2004_02
Patent number
US06686357B1

Reaction notes

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