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

HRID 1712649노트

반응식

HRID 1712649 반응식
[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

참가 물질

6

반응물 4

HCID 962Water2회HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 446076271-tert-Butyl 3-methyl azetidine-1,3-dicarboxylate

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-54b5aa80f3374815a51e11013d9e45a9
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07790885B2

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