تفاعل #10613

ord-b811f8e37f91454ca9c82dfe2654d854

معادلة التفاعل

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

المتفاعلات

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

الكواشف

لا شيء

المذيبات

CN(C)C=O
dimethylformamide

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  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
    أخرىthe deposited precipitates
  4. 4
    ترشيحwere collected by filtration
  5. 5
    غسيلThen, the precipitates were washed with water

الإجراء التجريبي

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).

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US07094789B2uspto-grants-2006_08