Triethylamine → HCID 57106621, compound

HRID 397658

Reaction equation

HRID 397658 reaction equation
C(N(CC)CC)C.Cl.[CH3:9][O:10][C:11]([C@@H:13]1[CH2:18][CH2:17][CH2:16][CH2:15][NH:14]1)=[O:12].[CH:19]1([CH2:25][S:26](Cl)(=[O:28])=[O:27])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1>ClCCl>[CH:19]1([CH2:25][S:26]([N:14]2[CH2:15][CH2:16][CH2:17][CH2:18][C@H:13]2[C:11]([O:10][CH3:9])=[O:12])(=[O:28])=[O:27])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 3871475Cyclohexylmethane sulfonyl chlorideHCID 13246232Methyl (2S)-piperidine-2-carboxylate--hydrogen chloride (1/1)

Product 1

HCID 57106621HCID 57106621, compoundYield 70.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (22.15 ml) was added to a solution of (2S)-2-(methoxycarbonyl)piperidine hydrochloride (10 g) [see Preparation 24] and cyclohexylmethanesulfonyl chloride (16.42 g) [King. J. F. et al,. J. Am. Chem. Soc., 1992, 114(5), 1743-9] in dichloromethane (100 ml). The reaction mixture was stirred for 18 hours after which time the solvent was removed under reduced pressure and the residue diluted with ethyl acetate. The organic layer was washed with water, brine, dried over magnesium sulphate and the solvent was removed under reduced pressure. The crude product was purified by column chromatography on silica gel eluting with a solvent gradient of 95:5 changing to 80:20, by volume, hexane:ethyl acetate to afford methyl (2S)-1-[(cyclohexylmethyl)sulfonyl]-2-piperidinecarboxylate (11.9 g) as a white solid.

Workup

  1. customwas removed under reduced pressure
  2. additionthe residue diluted with ethyl acetate
  3. washThe organic layer was washed with water, brine
  4. dry with materialdried over magnesium sulphate
  5. customthe solvent was removed under reduced pressure
  6. customThe crude product was purified by column chromatography on silica gel eluting with a solvent gradient of 95:5 changing to 80:20, by volume, hexane

Sources & evidence

ORD record
ord-8fae7256d29a449793106bcdde891b9f
Source dataset
uspto-grants-2003_08
Patent number
US06610707B1

Linked notes

Loading…