Trimethylsilyldiazomethane → 1-N-Boc-4-Piperidinecarboxylic acid methyl ester

HRID 8743

Reaction equation

HRID 8743 reaction equation
[C:1]([N:8]1[CH2:16][CH2:15][CH:11]([C:12]([OH:14])=[O:13])[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH3:17][Si](C=[N+]=[N-])(C)C>ClCCl.CO>[C:4]([O:3][C:1]([N:8]1[CH2:16][CH2:15][CH:11]([C:12]([O:14][CH3:17])=[O:13])[CH2:10][CH2:9]1)=[O:2])([CH3:7])([CH3:6])[CH3:5]

Participants

4

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 3928711-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acid

Product 1

HCID 3928701-N-Boc-4-Piperidinecarboxylic acid methyl esterYield 96.6%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

To a solution of BOC-isonipecotic acid (45.0 g, 0.20 mol) dissolved in a 3:1 solution of dichloromethane/methanol (1200 mL) at 0° C. was added a solution of trimethylsilyldiazomethane (147 mL, 0.29 mol, 2.0M in hexane) over 30 min via an addition funnel. The reaction mixture was then concentrated to afford the title compound (47 g) as a light yellow oil. This was used directly in the next step without further purification.

Workup

  1. concentrationThe reaction mixture was then concentrated

Sources & evidence

ORD record
ord-b2d23674e1954e95b0862e72fba9eb4a
Source dataset
uspto-grants-2006_08
Patent number
US07091211B2

Linked notes

Loading…