tert-Butyl ((1-benzylpyrrolidin-3-yl)methyl)carbamate → 1-(1-benzylpyrrolidin-3-yl)-N-methylmethanamine

HRID 1295870노트

반응식

HRID 1295870 반응식
[H-].[H-].[H-].[H-].[Li+].[Al+3].C(O[C:12](=O)[NH:13][CH2:14][CH:15]1[CH2:19][CH2:18][N:17]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:16]1)(C)(C)C>C1COCC1>[CH2:20]([N:17]1[CH2:18][CH2:19][CH:15]([CH2:14][NH:13][CH3:12])[CH2:16]1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

참가 물질

4

반응물 2

HCID 5108694tert-Butyl ((1-benzylpyrrolidin-3-yl)methyl)carbamateHCID 21226445Aluminium lithium hydride

생성물 1

HCID 46608321-(1-benzylpyrrolidin-3-yl)-N-methylmethanamine수율 90%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-5 °C

실험 절차

To a cooled (−5° C.) and stirred solution of LAH (1 M, 7.6 ml) in dry THF (75 ml) was added a solution of (1-benzyl-pyrrolidin-3-ylmethyl)-carbamic acid tert-butyl ester (1.47 g, 5.06 mmol) in THF (22 ml) over 20 minutes. The mixture was then heated at reflux for 2.5 hrs and cooled to room temperature and quenched by successive addition of ethyl acetate (50 ml). The organic layer was then washed with water (2×), 10% NaOH and brine, dried and evaporated to give the desired product in 90% yield.

후처리

  1. temperatureThe mixture was then heated
  2. temperatureat reflux for 2.5 hrs
  3. temperaturecooled to room temperature
  4. customquenched by successive addition of ethyl acetate (50 ml)
  5. washThe organic layer was then washed with water (2×), 10% NaOH and brine
  6. customdried
  7. customevaporated

출처 및 근거

ORD 기록
ord-26bde80f474c4806bddca5de0ac9e020
출처 데이터셋
uspto-grants-2007_07
특허 번호
US07244758B2

반응 노트

불러오는 중…