Methyl 1-((tert-butoxycarbonyl)amino)cyclopropanecarboxylate → tert-butyl N-(1-(hydroxymethyl)cyclopropyl)carbamate

HRID 539969ノート

反応式

HRID 539969 の反応式
[C:1]([O:5][C:6]([NH:8][C:9]1([C:12](OC)=[O:13])[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Li+]>O1CCCC1>[OH:13][CH2:12][C:9]1([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:3])([CH3:2])[CH3:4])[CH2:10][CH2:11]1

参加物

4

反応物 2

HCID 546046Methyl 1-((tert-butoxycarbonyl)amino)cyclopropanecarboxylateHCID 4148881Lithium borohydride

生成物 1

HCID 11286907tert-butyl N-(1-(hydroxymethyl)cyclopropyl)carbamate収率 76.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a cooled solution of methyl 1-[(tert-butoxycarbonyl)amino]cyclopropanecarboxylate (1.2 g, 5.6 mmol) in tetrahydrofuran (10 mL) at 0° C. was added dropwise a solution of lithium borohydride (244 mg, 11.2 mmol) in tetrahydrofuran (10 mL) The reaction mixture was allowed to warm to room temperature and stirred at this temperature overnight. The reaction was quenched by addition of water (10 mL) and the resulting mixture was extracted with dichloromethane. The organic layer was dried over sodium sulfate and concentrated in vacuo to afford 0.8 g of the product (yield was 76.2%).

後処理

  1. customThe reaction was quenched by addition of water (10 mL)
  2. extractionthe resulting mixture was extracted with dichloromethane
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-3965613a7bc948b996b16850d8fb5a03
出典データセット
uspto-grants-2014_10
特許番号
US08871756B2

反応ノート

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