(2S)-1-((tert-butoxy)carbonyl)piperidine-2-carboxylic acid → HCID 54019480, compound

HRID 1635646Notes

Reaction equation

HRID 1635646 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C@H:9]1[C:14]([OH:16])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:17][C@H:18]1[CH2:23][CH2:22][CH2:21][C@@H:20]([CH3:24])[N:19]1[CH2:25][CH2:26][NH2:27]>>[CH3:17][C@H:18]1[CH2:23][CH2:22][CH2:21][C@@H:20]([CH3:24])[N:19]1[CH2:25][CH2:26][NH:27][C:14]([C@@H:9]1[CH2:10][CH2:11][CH2:12][CH2:13][N:8]1[C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])=[O:16]

Participants

3

Reactant 2

HCID 688617(2S)-1-((tert-butoxy)carbonyl)piperidine-2-carboxylic acidHCID 7837022-(cis-2,6-Dimethyl-1-piperidinyl)ethanamine

Product 1

HCID 54019480HCID 54019480, compound

Procedure

The title compound was prepared by a similar method to Preparation 4 from (2S)-1-(tert butoxycarbonyl)-2-piperidinecarboxylic acid [see Preparation 13] and 2-[(cis)-2,6-dimethyl-1-piperidinyl]ethylamine [J. Med. Chem., 27; 5, (1984), 684-691]. The crude product was purified by column chromatography on silica gel eluting with a solvent gradient of 100:0 changing to 92:8, by volume, dichloromethane:methanol/0.88 aqueous ammonia solution (20/1), in 1% increments to afford tert-butyl (2S)-2-[(2-[(cis)-2,6-dimethyl-1-piperidinyl]ethylamino)carbonyl]-1-piperidinecarboxylate as an oil.

Workup

  1. customThe crude product was purified by column chromatography on silica gel eluting with a solvent gradient of 100:0 changing to 92:8, by volume, dichloromethane

Sources & evidence

ORD record
ord-c367120aa4cf48afae53af119ef1a311
Source dataset
uspto-grants-2003_01
Patent number
US06509464B1

Reaction notes

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