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

HRID 1852764Notes

Reaction equation

HRID 1852764 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 APCI 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-d7c137db846149568c502a7e233e784b
Source dataset
uspto-grants-2015_02
Patent number
US08962611B2

Reaction notes

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