Tert-butyl 3-(benzyloxycarbonylamino)-4-hydroxy-pyrrolidine-1-carboxylate → 1-Methyl-4-(methylamino)pyrrolidin-3-OL

HRID 1783606노트

반응식

HRID 1783606 반응식
[H-].[H-].[H-].[H-].[Li+].[Al+3].C(O[C:12]([N:14]1[CH2:18][CH:17]([OH:19])[CH:16]([NH:20][C:21](OCC2C=CC=CC=2)=O)[CH2:15]1)=O)(C)(C)C>C1COCC1>[CH3:12][N:14]1[CH2:15][CH:16]([NH:20][CH3:21])[CH:17]([OH:19])[CH2:18]1

참가 물질

4

반응물 2

HCID 20691380Tert-butyl 3-(benzyloxycarbonylamino)-4-hydroxy-pyrrolidine-1-carboxylateHCID 21226445Aluminium lithium hydride

생성물 1

HCID 684650761-Methyl-4-(methylamino)pyrrolidin-3-OL수율 18%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

LAH (1.40 g, 35.0 mmol) is slowly added to a stirred solution of 3-benzyloxycarbonylamino-4-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester in THF (15 ml) at room temperature. The reaction mixture is heated to reflux under N2 for 2 hours and then cooled to 0° C. The reaction mixture is quenched by the slow addition of Na2SO4.10 H2O, warmed to room temperature, diluted with ethyl acetate and filtered through Celite. The filtrate is concentrated and purified on a silica gel column (10:1:0.5 methylene chloride, MeOH, 30% NH4OH solution) to yield 0.21 g (18% for two steps) 1-methyl-4-methylamino-pyrrolidin-3-ol.

후처리

  1. temperatureThe reaction mixture is heated
  2. temperatureto reflux under N2 for 2 hours
  3. customThe reaction mixture is quenched by the slow addition of Na2SO4
  4. temperature10 H2O, warmed to room temperature
  5. additiondiluted with ethyl acetate
  6. filtrationfiltered through Celite
  7. concentrationThe filtrate is concentrated
  8. custompurified on a silica gel column (10:1:0.5 methylene chloride, MeOH, 30% NH4OH solution)

출처 및 근거

ORD 기록
ord-010bd08ef7d143ec9d0b4a56a6da7160
출처 데이터셋
uspto-grants-2009_03
특허 번호
US07501427B2

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