Triethylamine → 2-(3,3-Difluoropiperidin-1-yl)acetic acid

HRID 58895Notes

Reaction equation

HRID 58895 reaction equation
C(N(CC)CC)C.Cl.[F:9][C:10]1([F:16])[CH2:15][CH2:14][CH2:13][NH:12][CH2:11]1.Br[CH2:18][C:19]([O:21]CC1C=CC=CC=1)=[O:20]>C(Cl)Cl>[F:9][C:10]1([F:16])[CH2:15][CH2:14][CH2:13][N:12]([CH2:18][C:19]([OH:21])=[O:20])[CH2:11]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62576Benzyl bromoacetateHCID 27583493,3-Difluoropiperidine hydrochloride

Product 1

HCID 1150153032-(3,3-Difluoropiperidin-1-yl)acetic acidYield 85.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (0.660 mL, 4.76 mmol) was added to a solution of 3,3-difluoropiperidine-HCl (500 mg, 3.17 mmol) and benzyl 2-bromoacetate (763 mg, 3.33 mmol) in methylene chloride (10 mL). The reaction mixture was stirred at ambient temperature for 2 h. The mixture was washed with 1 N aqueous sodium hydroxide and water, successively. The organic layer was concentrated and the residue was purified by flash column chromatography on silica gel (Hexane/EtOAc=25:1) to afford benzyl ester of 2-(3,3-difluoropiperidin-1-yl)acetic acid (486 mg, 56% yield) as a yellow oil.

Workup

  1. washThe mixture was washed with 1 N aqueous sodium hydroxide and water
  2. concentrationThe organic layer was concentrated
  3. customthe residue was purified by flash column chromatography on silica gel (Hexane/EtOAc=25:1)

Sources & evidence

ORD record
ord-aa02993afa7944bfbd00611719bc537a
Source dataset
uspto-grants-2016_09
Patent number
US09434761B2

Reaction notes

Loading…