Benzaldehyde → (S)-2-(Benzylamino)propan-1-ol

HRID 1374978Notes

Reaction equation

HRID 1374978 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[NH2:15][C@@H:16]([CH3:19])[CH2:17][OH:18].[CH:20](=O)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>ClCCl.C(O)(=O)C>[CH2:20]([NH:15][C@@H:16]([CH3:19])[CH2:17][OH:18])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 3

HCID 240BenzaldehydeHCID 80307L-AlaninolHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 5356540(S)-2-(Benzylamino)propan-1-ol

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

Sodium triacetoxyborohydride (36.7 g) was added portion wisely to a mixture of (2S)-2-amino-1-propanol (10.0 g) and benzaldehyde (13.53 ml) in a mixture of dichloromethane (140 ml) and acetic acid (8.38 ml) at 0° C. and the whole was stirred at room temperature overnight. The mixture was washed successively with 2N sodium hydroxide and brine, and dried over sodium sulfate. The solution was evaporated under reduced pressure and the resulting residue was purified by column chromatography on silica gel using a mixed solvent of dichloromethane and methanol (30:1). The fractions containing the objective compound were collected and evaporated under reduced pressure to give (2S)-2-benzylamino-1-propanol (15.96 g).

Workup

  1. washThe mixture was washed successively with 2N sodium hydroxide and brine
  2. dry with materialdried over sodium sulfate
  3. customThe solution was evaporated under reduced pressure
  4. customthe resulting residue was purified by column chromatography on silica gel using a mixed solvent of dichloromethane and methanol (30:1)
  5. additionThe fractions containing the objective compound
  6. customwere collected
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-5428652c359045119c3877e3b9967944
Source dataset
uspto-grants-2007_01
Patent number
US07166598B2

Reaction notes

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