2-Chloro-1,3-benzoxazol-6-yl acetate → benzyl (2S)-1-[6-(acetyloxy)-1,3-benzoxazol-2-yl]-2-piperidinecarboxylate
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.[C:18]([O:21][C:22]1[CH:31]=[CH:30][C:25]2[N:26]=[C:27](Cl)[O:28][C:24]=2[CH:23]=1)(=[O:20])[CH3:19]>>[C:18]([O:21][C:22]1[CH:31]=[CH:30][C:25]2[N:26]=[C:27]([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])[O:28][C:24]=2[CH:23]=1)(=[O:20])[CH3:19]Participants
3
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] from 2-chloro-1,3-benzoxazol-6-yl acetate [see Preparation 35]. The crude product was purified by column chromatography on silica gel eluting with a solvent gradient of 80:10 changing to 40:10, by volume, hexane:ethyl acetate to afford benzyl (2S)-1-[6-(acetyloxy)-1,3-benzoxazol-2-yl]-2-piperidinecarboxylate as a gum.
Workup
- customThe crude product was purified by column chromatography on silica gel eluting with a solvent gradient of 80:10 changing to 40:10, by volume, hexane
Sources & evidence
- ORD record
- ord-bc823bbbbd9a4866a9302d699bee213c
- Source dataset
- uspto-grants-2000_12
- Patent number
- US06166011
Reaction notes
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