Dimethylformamide → HCID 86705548, 화합물

HRID 2279563노트

반응식

HRID 2279563 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[C:19]([Cl:24])[CH:18]=2)(C(O)=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)=CC=1.C[N:43]([CH:45]=[O:46])C>CCOC(C)=O>[Cl:24][C:19]1[CH:18]=[C:17]([C:11]2([N:43]=[C:45]=[O:46])[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:3])([CH3:2])[CH3:4])=[O:7])[CH2:9][CH2:10]2)[CH:22]=[CH:21][C:20]=1[Cl:23]

참가 물질

5

반응물 3

HCID 6228DimethylformamideHCID 199401P,P-Diphenylphosphinic azideHCID 68294367HCID 68294367, 화합물

생성물 1

HCID 86705548HCID 86705548, 화합물수율 91%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

To a stirred solution of 358 (187 mg, 0.4997 mmol) in DMF (1.5 mL) at RT under nitrogen was added TEA (167.1 μL, 1.199 mmol) neat via syringe followed by DPPA (129.6 μL, 0.5996 mmol) neat by syringe. The solution was stirred for 2 h at RT then warmed to 60° C. After 3 h at 60° C., the reaction was cooled to RT and diluted to 30 mL with EtOAc. The organic extract was washed with H2O (3×30 mL) and brine (1×30 mL). The organics were dried (MgSO4), filtered and concentrated to afford 170 mg (91%) of tert-butyl 4-(3,4-dichlorophenyl)-4-isocyanatopiperidine-1-carboxylate (360) as a clear oil.

후처리

  1. temperaturethen warmed to 60° C
  2. waitAfter 3 h at 60° C.
  3. temperaturethe reaction was cooled to RT
  4. extractionThe organic extract
  5. washwas washed with H2O (3×30 mL) and brine (1×30 mL)
  6. dry with materialThe organics were dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-8458255fded8411681fa1631e944df46
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09133187B2

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