Ammonia → HCID 67228863, compound

HRID 1026118Notes

Reaction equation

HRID 1026118 reaction equation
C[O:2][C:3](=O)[C@@H:4]([NH:15]C(OCC1C=CC=CC=1)=O)[CH2:5][O:6][CH:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH3:8].N>CO.[Pd]>[NH2:15][C@@H:4]([CH2:5][O:6][CH:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH3:8])[CH2:3][OH:2]

Participants

5

Reactant 2

HCID 222AmmoniaHCID 67177433HCID 67177433, compound

Product 1

HCID 67228863HCID 67228863, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

To a solution of (S)-2-benzyloxycarbonylamino-3-(1-phenyl-ethoxy)-propionic acid methyl ester (1.1 g) in methanol (5 ml) were added ammonia in methanol (7 N solution, 0.22 ml) and palladium on charcoal (5%, 110 mg). The mixture was stirred vigorously under an atmosphere of hydrogen for 30 min. The catalyst was filtered off and the filtrate was evaporated. The crude product was purified by column chromatography (SiO2; dichloromethane/MeOH=98:2) to give (R)-2-amino-3-(1-phenyl-ethoxy)-propan-1-ol (280 mg, 86%) as a light yellow liquid. MS (ISP): 224.2 ([M+H]+)).

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate was evaporated
  3. customThe crude product was purified by column chromatography (SiO2; dichloromethane/MeOH=98:2)

Sources & evidence

ORD record
ord-26dbebee2aa64c48889b2db4c2ea8922
Source dataset
uspto-grants-2014_05
Patent number
US08729113B2

Reaction notes

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