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

HRID 44241

反応式

HRID 44241 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
80 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-ae2107d120a34bfc8fc62b7007f33355
出典データセット
uspto-grants-2013_09
特許番号
US08541407B2

関連ノート

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