Water → tert-Butyl 3-(hydroxymethyl)azetidine-1-carboxylate

HRID 1712649ノート

反応式

HRID 1712649 の反応式
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([O:11][C:12]([N:14]1[CH2:17][CH:16]([C:18](OC)=[O:19])[CH2:15]1)=[O:13])([CH3:10])([CH3:9])[CH3:8].O.[OH-].[Na+]>O1CCCC1>[OH:19][CH2:18][CH:16]1[CH2:17][N:14]([C:12]([O:11][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:13])[CH2:15]1

参加物

6

反応物 4

HCID 962Water2 回HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 446076271-tert-Butyl 3-methyl azetidine-1,3-dicarboxylate

生成物 1

HCID 10583745tert-Butyl 3-(hydroxymethyl)azetidine-1-carboxylate収率 95.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

Lithium aluminium hydride (128 mg) was placed in a round bottomed flask, and suspended in tetrahydrofuran (30 ml). The suspension was cooled in an ice bath, and a solution of methyl 1-tert-butoxycarbonylazetidine-3-carboxylate (970 mg) in tetrahydrofuran (10 ml) was added gradually, followed by stirring at the same temperature under a nitrogen atmosphere for 1 hour. Water (0.13 ml), a 5N aqueous solution of sodium hydroxide (0.13 ml) and water (0.39 ml) was added to the reaction mixture with cooling in an ice bath, followed by stirring at the same temperature for 1 hour. Insoluble matter in the reaction mixture was removed by filtration. The filtrate was concentrated to give the title compound (805 mg, 95.3%) as a colorless oil.

後処理

  1. temperatureThe suspension was cooled in an ice bath
  2. temperaturewith cooling in an ice bath
  3. stirringby stirring at the same temperature for 1 hour
  4. customInsoluble matter in the reaction mixture was removed by filtration
  5. concentrationThe filtrate was concentrated

出典と根拠

ORDレコード
ord-54b5aa80f3374815a51e11013d9e45a9
出典データセット
uspto-grants-2010_09
特許番号
US07790885B2

反応ノート

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