tert-Butanol → Tert-butyl (1-(4-chlorophenyl)cyclopropyl)carbamate

HRID 44241

반응식

HRID 44241 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2(C(O)=O)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.C([N:16]([CH2:19]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:28])C=CC=CC=1.[C:38]([OH:42])([CH3:41])([CH3:40])[CH3:39]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([NH:16][C:19](=[O:28])[O:42][C:38]([CH3:41])([CH3:40])[CH3:39])[CH2:9][CH2:10]2)=[CH:6][CH:7]=1

참가 물질

6

반응물 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 986061-(p-Chlorophenyl)cyclopropanecarboxylic acidHCID 199401P,P-Diphenylphosphinic azide

생성물 1

HCID 58458569Tert-butyl (1-(4-chlorophenyl)cyclopropyl)carbamate

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
80 °C

실험 절차

A solution of 1-(4-chlorophenyl)cyclopropanecarboxylic acid (10.5 g, 53.3 mmol) in toluene (70 mL) was treated successively with triethylamine (15 mL, 106.6 mmol), diphenylphosphorylazide (DPPA) (12.7 mL, 58.6 mmol) and tert-butanol (25 mL, 267 mmol). The reaction mixture was stirred at 80° C. for 20 hours. The mixture was partitioned between ethyl acetate (300 mL) and water (100 mL). The phases were separated and the organic phase was washed with water (80 mL) then brine (100 mL). The organic phase was dried over sodium sulfate, filtered and concentrated in vacuo. The crude product was purified by flash chromatography (SiO2, 10% ethyl acetate in hexanes). The tert-butyl (1-(4-chlorophenyl)cyclopropyl)carbamate was obtained as a white solid (14 g). LCMS [M+H]: 268.

후처리

  1. customThe mixture was partitioned between ethyl acetate (300 mL) and water (100 mL)
  2. customThe phases were separated
  3. washthe organic phase was washed with water (80 mL)
  4. dry with materialThe organic phase was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by flash chromatography (SiO2, 10% ethyl acetate in hexanes)

출처 및 근거

ORD 기록
ord-ae2107d120a34bfc8fc62b7007f33355
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08541407B2

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