反応 #10613

ord-b811f8e37f91454ca9c82dfe2654d854

反応方程式

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

反応物

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

試薬

なし

溶媒

CN(C)C=O
dimethylformamide

反応条件

詳細条件
See reaction.notes.procedure_details.

後処理

  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
    その他the deposited precipitates
  4. 4
    ろ過were collected by filtration
  5. 5
    洗浄Then, the precipitates were washed with water

実験手順

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).

出典

DOI: 10.6084/m9.figshare.5104873.v1特許: US07094789B2uspto-grants-2006_08