Methylamine → Tert-butyl 3-hydroxy-4-(methylamino)pyrrolidine-1-carboxylate

HRID 423414노트

반응식

HRID 423414 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]2[CH:10]([O:11]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:14][NH2:15]>C(=O)(O)[O-].[Na+]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]([NH:15][CH3:14])[CH:10]([OH:11])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

참가 물질

4

반응물 2

HCID 6329MethylamineHCID 10103880tert-Butyl 6-Oxa-3-azabicyclo(3.1.0)hexane-3-carboxylate

생성물 1

HCID 21736783Tert-butyl 3-hydroxy-4-(methylamino)pyrrolidine-1-carboxylate수율 97%

시약·촉매·용매 1

HCID 516892Sodium Bicarbonate용매

반응 조건

온도
50 °C

실험 절차

Dissolve 6-oxa-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid tert-butyl ester (1.50 g, 8.10 mmol) in methylamine (15 mL, 40% solution in water). Warm to 50° C. and stir in a sealed vessel overnight. Dilute the mixture with saturated sodium bicarbonate and extract with dichloromethane (3×). Dry the organics over sodium sulfate, filter, and evaporate. Purify by silica gel chromatography, eluting with 0-10% methanol (2N NH3)/CH2Cl2 to give 1.87 g (97%) of 3-hydroxy-4-methylamino-pyrrolidine-1-carboxylic acid tert-butyl ester as a yellow oil.

후처리

  1. extractionextract with dichloromethane (3×)
  2. dry with materialDry the organics over sodium sulfate
  3. filtrationfilter
  4. customevaporate
  5. customPurify by silica gel chromatography
  6. washeluting with 0-10% methanol (2N NH3)/CH2Cl2

출처 및 근거

ORD 기록
ord-e3f1435a1e1d472e994213bbe0edb102
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08101764B2

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