반응 #10613

ord-b811f8e37f91454ca9c82dfe2654d854

반응 방정식

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

반응물

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

시약

없음

용매

CN(C)C=O
dimethylformamide

반응 조건

상세 조건
See reaction.notes.procedure_details.

후처리

  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
    기타the deposited precipitates
  4. 4
    여과were collected by filtration
  5. 5
    세척Then, the precipitates were washed with water

실험 절차

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).

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US07094789B2uspto-grants-2006_08