Benzyl chloroformate → HCID 67490844, compound

HRID 1917373Notes

Reaction equation

HRID 1917373 reaction equation
Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].[CH3:12][O:13][C:14]([C@@:16]12[CH2:24][N:23](CC3C=CC=CC=3)[CH2:22][C@@H:21]1[CH2:20][CH2:19][CH2:18][CH2:17]2)=[O:15]>ClCCl>[CH3:12][O:13][C:14]([C@@:16]12[CH2:24][N:23]([C:2]([O:4][CH2:5][C:6]3[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=3)=[O:3])[CH2:22][C@@H:21]1[CH2:20][CH2:19][CH2:18][CH2:17]2)=[O:15]

Participants

4

Reactant 2

HCID 10387Benzyl chloroformateHCID 6558968HCID 6558968, compound

Product 1

HCID 67490844HCID 67490844, compoundYield 70.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Benzyl chloroformate (33.4 mL, 234 mmol) was added to a solution of [(1R*,6R*)-8-benzyl-8-azabicyclo[4.3.0]nonan-1-yl]carboxylic acid methyl ester (21.3 g, 77.9 mmol) in dichloromethane (259 mL) in a nitrogen atmosphere, and the mixture was stirred at room temperature for 15 hours. The reaction solution was concentrated under reduced pressure. Then, the residue (58.0 g) was purified by silica gel column chromatography (hexane:ethyl acetate=100:0→95:5→90:10→80:20→75:25) to give 17.5 g of the title compound.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. customThen, the residue (58.0 g) was purified by silica gel column chromatography (hexane:ethyl acetate=100:0→95:5→90:10→80:20→75:25)

Sources & evidence

ORD record
ord-28cdaa6eaf1c47c0a31ee6faf5fc4bf0
Source dataset
uspto-grants-2013_12
Patent number
US08618094B2

Reaction notes

Loading…