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

HRID 81156

Reaction equation

HRID 81156 reaction equation
[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

Participants

5

Reactant 2

HCID 7504BenzylamineHCID 92446-Oxabicyclo[3.1.0]hexane

Product 1

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

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-531e70f09f494af19da5601ed546dc0a
Source dataset
uspto-grants-2014_09
Patent number
US08846657B2

Linked notes

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