Benzyl chloroformate → Benzyl N-[(oxolan-3-yl)methyl]carbamate

HRID 624219

反応式

HRID 624219 の反応式
[O:1]1[CH2:5][CH2:4][CH:3]([CH2:6][NH2:7])[CH2:2]1.C(N(C(C)C)CC)(C)C.[C:17](Cl)(=[O:26])[O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>ClCCl>[O:1]1[CH2:5][CH2:4][CH:3]([CH2:6][NH:7][C:17](=[O:26])[O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:2]1

参加物

5

反応物 3

HCID 10387Benzyl chloroformateHCID 81531DiisopropylethylamineHCID 10898660(Tetrahydrofuran-3-yl)methanamine

生成物 1

HCID 86665085Benzyl N-[(oxolan-3-yl)methyl]carbamate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
0 °C

実験手順

Racemic (tetrahydrofuran-3-yl)methanamine (3.84 g, 38.0 mmol) and diisopropylethylamine (13.26 ml, 76 mmol), were dissolved in dichloromethane (100 ml) and cooled to 0° C. The mixture was treated dropwise via an addition funnel with benzyl carbonochloridate (6.19 ml, 41.8 mmol) dissolved in 30 ml dichlormethane. After the addition the cooling bath was removed and the homogeneous solution was stirred at ambient temperature overnight. The reaction mixture was partitioned between water and ethyl acetate and the separated aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered and concentrated. Chromatography provided the title compound.

後処理

  1. additionAfter the addition the cooling bath
  2. customwas removed
  3. customThe reaction mixture was partitioned between water and ethyl acetate
  4. extractionthe separated aqueous layer was extracted with ethyl acetate
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-0331e16ad7c94a6790ff51d42215f4f7
出典データセット
uspto-grants-2016_04
特許番号
US09302989B2

関連ノート

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