Phenacyl bromide → (RS)-2-[2-phenyl-2-oxo-ethoxycarbonylmethyl]-piperidine-1-carboxylic tert butyl ester

HRID 549333Notes

Reaction equation

HRID 549333 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14][C:15]([OH:17])=[O:16])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[Na+].[Na+].Br[CH2:25][C:26]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:27]>O.C(O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14][C:15]([O:17][CH2:25][C:26](=[O:27])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:16])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 6259Phenacyl bromideHCID 10340Sodium CarbonateHCID 50585361-Boc-2-Piperidineacetic Acid

Product 1

HCID 86629005(RS)-2-[2-phenyl-2-oxo-ethoxycarbonylmethyl]-piperidine-1-carboxylic tert butyl esterYield 74.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

2-Carboxymethyl-piperidine-1-carboxylic acid tert butyl ester (2.86 g) and sodium carbonate (0.62 g) were dissolved in water (30 ml) using gentle warming. A solution of 2-bromoacetophenone (2.33 g) in ethanol (60 ml) was then added and the mixture boiled for 2 h. the mixture was cooled to room temperature and stood for 16 h. The mixture was again boiled for 2 h. solvent removed at reduced pressure and the residue partitioned between water and ethyl acetate. The organic phase was dried (MgSO4) and solvent removed at reduced pressure. The residue was column chromatographed (silica gel, 1:1 ethyl acetate:pentane) to give the title compound (3.14 g).

Workup

  1. waitstood for 16 h
  2. waitThe mixture was again boiled for 2 h.
  3. customsolvent removed at reduced pressure
  4. customthe residue partitioned between water and ethyl acetate
  5. dry with materialThe organic phase was dried (MgSO4) and solvent
  6. customremoved at reduced pressure
  7. customchromatographed (silica gel, 1:1 ethyl acetate:pentane)

Sources & evidence

ORD record
ord-d1c3a0ed70b44a95a9d8b2283907f59e
Source dataset
uspto-grants-2011_05
Patent number
US07943645B2

Reaction notes

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