(2S)-1-(1,3-benzoxazol-2-yl)-2-piperidinecarboxylic acid → Ammonia

HRID 1276163Notes

Reaction equation

HRID 1276163 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[N:10]1[CH2:15][CH2:14][CH2:13][CH2:12][C@H:11]1[C:16]([OH:18])=O.[NH2:19][CH2:20][CH2:21][N:22]1[C@@H:27]([CH3:28])[CH2:26][N:25]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:24][C@H:23]1[CH3:36]>>[NH3:3].[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[N:10]1[CH2:15][CH2:14][CH2:13][CH2:12][C@H:11]1[C:16]([NH:19][CH2:20][CH2:21][N:22]1[C@@H:27]([CH3:28])[CH2:26][N:25]([C:29]([O:31][C:32]([CH3:33])([CH3:35])[CH3:34])=[O:30])[CH2:24][C@H:23]1[CH3:36])=[O:18]

Participants

4

Reactant 2

HCID 12050655(2S)-1-(1,3-benzoxazol-2-yl)-2-piperidinecarboxylic acidHCID 53985942Tert-butyl(cis)-4-(2-aminoethyl)-3,5-dimethyl-1-piperazinecarboxylate

Product 2

HCID 222AmmoniaHCID 12096137tert-butyl (cis)-4-[2-([(2S)-1-(1,3-benzoxazol-2-yl)-2-piperidinyl]carbonylamino)ethyl]-3,5-dimethyl-1-piperazinecarboxylate

Procedure

The title compound was prepared by a similar method to Preparation 4 from (2S)-1-(1,3-benzoxazol-2-yl)-2-piperidinecarboxylic acid [see Preparation 3] and tert-butyl (cis)-4-(2-aminoethyl)-3,5-dimethyl-1-piperazinecarboxylate [see Preparation 7]. The crude product was purified by column chromatography on silica gel eluting with a solvent gradient of 4:1:0 changing to 93:7:1, by volume, dichoromethane:methanol:0.88 aqueous ammonia solution in 1% increments to afford tert-butyl (cis)-4-[2-([(2S)-1-(1,3-benzoxazol-2-yl)-2-piperidinyl]carbonylamino)ethyl]-3,5-dimethyl-1-piperazinecarboxylate as an oil.

Workup

  1. customThe crude product was purified by column chromatography on silica gel eluting with a solvent gradient of 4:1:0 changing to 93:7:1, by volume, dichoromethane

Sources & evidence

ORD record
ord-23aa3bb2cdf8492f84324ef1c7f2561a
Source dataset
uspto-grants-2000_12
Patent number
US06166011

Reaction notes

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