Benzaldehyde → (R)-Methyl 2-(benzylamino)-3-hydroxypropanoate

HRID 629691Notes

Reaction equation

HRID 629691 reaction equation
[Cl-].[OH:2][CH2:3][C@@H:4]([NH3+:9])[C:5]([O:7][CH3:8])=[O:6].C(N(CC)CC)C.[CH:17](=O)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[BH4-].[Na+].[NH4+].[Cl-]>CO.CCOC(C)=O>[CH2:17]([NH:9][C@@H:4]([C:5]([O:7][CH3:8])=[O:6])[CH2:3][OH:2])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

8

Reactant 5

HCID 240BenzaldehydeHCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 10964746[(2R)-3-Hydroxy-1-methoxy-1-oxopropan-2-yl]azanium;chloride

Product 1

HCID 11063677(R)-Methyl 2-(benzylamino)-3-hydroxypropanoate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To (2R)-3-hydroxy-1-methoxy-1-oxopropan-2-aminium chloride (1 eq.) in MeOH (1.3 M) at 0° C. was added triethylamine (1 eq.). The reaction mixture was stirred for 10 minutes and benzaldehyde (1 eq) was added. The reaction mixture was stirred for 2 hours and NaBH4 (1.5 eq.) was added portionwise to the reaction mixture over 30 min. The reaction mixture was stirred at rt for 5 hours and poured into a 1:1 mixture of saturated aqueous NH4Cl and EtOAc. The aqueous layer was extracted with EtOAc and the combined organic layers were washed with brine and water, dried over Na2SO4, filtered and concentrated. The crude product was used as such for the next step.

Workup

  1. stirringThe reaction mixture was stirred for 2 hours
  2. stirringThe reaction mixture was stirred at rt for 5 hours
  3. extractionThe aqueous layer was extracted with EtOAc
  4. washthe combined organic layers were washed with brine and water
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-6beb0fbf45e2459295d595bed8fd07f4
Source dataset
uspto-grants-2016_04
Patent number
US09315475B2

Reaction notes

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