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

HRID 81156

反応式

HRID 81156 の反応式
[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

参加物

5

反応物 2

HCID 7504BenzylamineHCID 92446-Oxabicyclo[3.1.0]hexane

生成物 1

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

試薬・触媒・溶媒 2

HCID 11026Titanium isopropoxide触媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-531e70f09f494af19da5601ed546dc0a
出典データセット
uspto-grants-2014_09
特許番号
US08846657B2

関連ノート

読み込み中…