Sodium Methoxide → HCID 68480332, compound

HRID 2191121Notes

Reaction equation

HRID 2191121 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH:7]1[C:19]1[CH:24]=[CH:23][C:22]([F:25])=[C:21]([F:26])[CH:20]=1)=[O:5])C.C[O-].[Na+]>CO>[CH3:1][O:3][C:4]([CH:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:16])[CH3:17])=[O:13])[CH2:8][CH:7]1[C:19]1[CH:24]=[CH:23][C:22]([F:25])=[C:21]([F:26])[CH:20]=1)=[O:5]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 68478083HCID 68478083, compound

Product 1

HCID 68480332HCID 68480332, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2.2 g (5.9 mmol) (3SR,4RS)-3-(3,4-Difluoro-phenyl)-piperidine-1,4-dicarboxylic acid 1-tert-butyl ester 4-ethyl ester and 0.18 mL NaOMe (5.4N in methanol) in 60 mL methanol was first stirred at room temperature and subsequently ar reflux until consumption of the starting material. The mixture was evaporated to dryness and the residue subjected to column chromatography on silica eluting with a gradient formed from ethyl acetate and heptane to afford after evaporation of the product containing fractions 1.5 g (71%) of the title compound as colorless oil. MS (m/e): 256.1 [(M+H-Boc)+].

Workup

  1. temperaturesubsequently ar reflux until consumption of the starting material
  2. customThe mixture was evaporated to dryness
  3. customformed from ethyl acetate and heptane
  4. customto afford
  5. customafter evaporation of the product
  6. additioncontaining fractions 1.5 g (71%) of the title compound as colorless oil

Sources & evidence

ORD record
ord-ec7be72973c14eb19dc99dc57d7256a5
Source dataset
uspto-grants-2012_12
Patent number
US08324248B2

Reaction notes

Loading…