Reaction #10613

ord-b811f8e37f91454ca9c82dfe2654d854

Reaction equation

O
water
CC(C)(C)OC(=O)N[C@H]1CC[C@H](OS(C)(=O)=O)CC1
Intermediate 36
CC(C)(C)OC(=O)N[C@H]1CC[C@H](OS(C)(=O)=O)CC1
trans-N-(tert-butoxycarbonyl)-N-(4-methanesulfonyloxycyclohexyl)amine
C[Si](C)(C)N=[N+]=[N-]
trimethylsilyl azide
[Cs+].[F-]
cesium fluoride
→
CC(C)(C)OC(=O)N[C@H]1CC[C@@H](N=[N+]=[N-])CC1
title compound
CC(C)(C)OC(=O)N[C@H]1CC[C@@H](N=[N+]=[N-])CC1
cis-4-(N-tert-butoxycarbonylamino)cyclohexyl azide

Reactants

O
water
CC(C)(C)OC(=O)N[C@H]1CC[C@H](OS(C)(=O)=O)CC1
Intermediate 36
CC(C)(C)OC(=O)N[C@H]1CC[C@H](OS(C)(=O)=O)CC1
trans-N-(tert-butoxycarbonyl)-N-(4-methanesulfonyloxycyclohexyl)amine
C[Si](C)(C)N=[N+]=[N-]
trimethylsilyl azide
[Cs+].[F-]
cesium fluoride

Reagents

None

Solvents

CN(C)C=O
dimethylformamide

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    workup.STIRRINGstirred at 70° C. for 4 days
  2. 2
    workup.STIRRINGThis reaction mixture was stirred with ice cooling for 2 hours
  3. 3
    Otherthe deposited precipitates
  4. 4
    Filtrationwere collected by filtration
  5. 5
    WashThen, the precipitates were washed with water

Procedure

A solution of Intermediate 36 (196 g) and trimethylsilyl azide (283 ml, Tokyo Kasei Kogyo) in dimethylformamide (667 ml) was added with cesium fluoride (305 g, Wako Pure Chemical Industries) with stirring and stirred at 70° C. for 4 days. The reaction mixture was cooled to room temperature and then added twice with water in a volume of 2.75 l in total. This reaction mixture was stirred with ice cooling for 2 hours, and the deposited precipitates were collected by filtration. Then, the precipitates were washed with water to obtain a roughly purified product of the title compound (142 g).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07094789B2uspto-grants-2006_08