phenylalaninol, (S)- → (S)-2-benzylamino-3-phenyl-1-propanol

HRID 1863916Notes

Reaction equation

HRID 1863916 reaction equation
[NH2:1][C@H:2]([CH2:10][OH:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[BH4-].[Na+]>CO>[CH2:3]([NH:1][C@H:2]([CH2:10][OH:11])[CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 447213phenylalaninol, (S)-HCID 4311764Sodium borohydride

Product 1

HCID 10514267(S)-2-benzylamino-3-phenyl-1-propanolYield 175.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of L-phenylalaninol 3c (where W=H, W=OH, R1=H, R2=Bn, R3=H) (5 g) in MeOH (150 ml) benzaldehyde (3.3 ml) were added. The reaction mixture was stirred at r.t. for 1 h, then 1.2 g of NaBH4, were added in small portions in 2 hr at 0° C. The solvent was evaporated and the residue extracted with 50 ml of HCl at pH=2. The aqueous solution was extracted with Et2O, treated with Na2CO3 until pH=9 and then extracted with CHCl3. The organic phase evaporated gave N-benzyl-(L)-phenylalaninol as white solid (7 g) 3c (where W=H, W=OH, R1=H, R2=Bn, R3=Bn)

Workup

  1. customThe solvent was evaporated
  2. extractionthe residue extracted with 50 ml of HCl at pH=2
  3. extractionThe aqueous solution was extracted with Et2O
  4. additiontreated with Na2CO3 until pH=9
  5. extractionextracted with CHCl3
  6. customThe organic phase evaporated

Sources & evidence

ORD record
ord-7da1dff1bc634b07907ae7e3018bfb57
Source dataset
uspto-grants-2009_12
Patent number
US07625892B2

Reaction notes

Loading…