Trimethylsilyldiazomethane → 4-(2-Diazo-acetyl)-piperidine-1-carboxylic acid benzyl ester

HRID 79731Notes

Reaction equation

HRID 79731 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([C:17](Cl)=[O:18])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Si]([CH:24]=[N+:25]=[N-:26])(C)C>ClCCl>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([C:17](=[O:18])[CH:24]=[N+:25]=[N-:26])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 2776270Benzyl 4-(chlorocarbonyl)piperidine-1-carboxylate

Product 1

HCID 866488824-(2-Diazo-acetyl)-piperidine-1-carboxylic acid benzyl esterYield 102.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Chlorocarbonyl-piperidine-1-carboxylic acid benzyl ester (43 g, 0.15 mol) in dichloromethane (300 mL) was treated with (trimethylsilyl)diazomethane (2.0 M in hexanes, 150 mL, 0.31 mol) over 15 min. The reaction mixture was stirred at ambient temperature for 18 hours and the mixture was concentrated to afford crude 4-(2-diazo-acetyl)-piperidine-1-carboxylic acid benzyl ester (44 g), which was used without further purification.

Workup

  1. concentrationthe mixture was concentrated

Sources & evidence

ORD record
ord-bcb28539ef314bbfb794c294be75dacd
Source dataset
uspto-grants-2014_09
Patent number
US08841278B2

Reaction notes

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