Benzylamine → (1R,2R)-2-(Benzylamino)cyclopentan-1-ol

HRID 81156

반응식

HRID 81156 반응식
[CH:1]12[O:6][CH:2]1[CH2:3][CH2:4][CH2:5]2.[CH2:7]([NH2:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>CCOC(C)=O.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[CH2:7]([NH:14][C@@H:2]1[CH2:3][CH2:4][CH2:5][C@H:1]1[OH:6])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

참가 물질

5

반응물 2

HCID 7504BenzylamineHCID 92446-Oxabicyclo[3.1.0]hexane

생성물 1

HCID 45382208(1R,2R)-2-(Benzylamino)cyclopentan-1-ol

시약·촉매·용매 2

HCID 11026Titanium isopropoxide촉매HCID 8857Ethyl Acetate용매

실험 절차

Cyclopentene oxide (5.0 g, 59.1 mmol), benzylamine (7.0 g, 65.3 mmol) and titanium isopropoxide (3.40 g, 12.0 mmol) were taken in a microwave vial and microwaved at 150° C. for 3 hours. The reaction mixture was then cooled and diluted with EtOAc (100 mL). The organic layer was washed with water and dried over anhydrous Na2SO4. Evaporation of the solvent in vacuo and purification on a silica gel column (0 to 20% MeOH/CH2Cl2) afforded trans-2-(benzylamino)cyclopentanol. MS APCl calc'd for C12H17NO [M+H]+ 192. found 192.

후처리

  1. custommicrowaved at 150° C. for 3 hours
  2. temperatureThe reaction mixture was then cooled
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous Na2SO4
  5. customEvaporation of the solvent
  6. customin vacuo and purification on a silica gel column (0 to 20% MeOH/CH2Cl2)

출처 및 근거

ORD 기록
ord-531e70f09f494af19da5601ed546dc0a
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846657B2

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