Benzyl chloroformate → benzyl N-(1-cyano-1-methylbutyl)carbamate

HRID 1486243ノート

反応式

HRID 1486243 の反応式
[NH2:1][C:2]([CH3:8])([CH2:5][CH2:6][CH3:7])[C:3]#[N:4].C(=O)([O-])[O-].[K+].[K+].Cl[C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17]>C1COCC1.O>[C:3]([C:2]([NH:1][C:16](=[O:17])[O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([CH2:5][CH2:6][CH3:7])[CH3:8])#[N:4]

参加物

5

反応物 3

HCID 10387Benzyl chloroformateHCID 11430Potassium CarbonateHCID 208880Pentanenitrile, 2-amino-2-methyl-

生成物 1

HCID 117861119benzyl N-(1-cyano-1-methylbutyl)carbamate収率 99.8%

試薬・触媒・溶媒 1

HCID 21881883Oxolane--water (1/1)溶媒

実験手順

20 g (178.3 mmol) of rac-2-amino-2-methylpentanonitrile (described in: Deng, S L. et al., Synthesis 2001, 2445-2449; Freifelder, M. et al., J. Am. Chem. Soc. 1960, 696-698) were initially charged in 2.63 l of THF/water (8/1), and 76.4 g (552.7 mmol) of potassium carbonate were added. Then 27.6 ml (196.1 mmol) of benzyl chloroformate were slowly added dropwise at 0° C. and the mixture was stirred at RT overnight. The reaction mixture was concentrated, and the residue was admixed with water and extracted twice with ethyl acetate. The combined organic phases were dried over sodium sulphate, filtered and concentrated. The residue was purified by means of silica gel chromatography (eluent:cyclohexane/ethyl acetate=4/1). 43.84 g of the target compound were obtained (76% of theory, 76% purity).

後処理

  1. concentrationThe reaction mixture was concentrated
  2. extractionextracted twice with ethyl acetate
  3. dry with materialThe combined organic phases were dried over sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by means of silica gel chromatography (eluent:cyclohexane/ethyl acetate=4/1)

出典と根拠

ORDレコード
ord-3d8858066dc04594ab0fef1838963295
出典データセット
uspto-grants-2016_08
特許番号
US09422285B2

反応ノート

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