Water → tert-Butyl 3-hydroxy-3-methylpyrrolidine-1-carboxylate

HRID 1496687노트

반응식

HRID 1496687 반응식
[C:1](=[C:3]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4]1)=O.C[Mg]I.[OH2:18]>C1COCC1.C(OCC)C>[OH:18][C:3]1([CH3:1])[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4]1

참가 물질

6

반응물 3

HCID 962WaterHCID 89961906HCID 89961906, 화합물HCID 178418373HCID 178418373, 화합물

생성물 1

HCID 22951485tert-Butyl 3-hydroxy-3-methylpyrrolidine-1-carboxylate

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매

실험 절차

A solution of tert-butyl 3-carbonylpyrrolidine-1-carboxylate (11.17 g, 0.06 mol) in THF (45 mL) was slowly added to a solution of MeMgI (21.41 g, 0.129 mol) in diethyl ether. The reaction was conducted at −20° C. under stirring for 3 hours. A small amount of water was added to the reaction solution. The resulting reaction solution was filtered by suction. The filtrate was extracted with dichloromethane. The organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated to produce a crude product of tert-butyl 3-hydroxy-3-methyl-pyrrolidine-1-carboxylate. The above crude product was dissolved in 20 mL 1,4-dioxane. To the resulting solution was introduced an HCl gas. The resulting mixute was stirred overnight and filtered by suction to produce the title product as a red solid (1.67 g) in a yield of 20% (two steps).

후처리

  1. customwas conducted at −20° C.
  2. customThe resulting reaction solution
  3. filtrationwas filtered by suction
  4. extractionThe filtrate was extracted with dichloromethane
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated

출처 및 근거

ORD 기록
ord-ffe69f0f6ac545d4883a0ee11ad5c282
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09198902B2

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