Chloroform → (1S,2S)-2-amino-3-morpholino-1-phenyl-1-propanol

HRID 1075696

Reaction equation

HRID 1075696 reaction equation
C(OC([NH:11][C@@H:12]([CH2:21][N:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1)[C@H:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[OH:14])=O)C1C=CC=CC=1.C([O-])=O.[NH4+].C(Cl)(Cl)Cl>CO.[C].[Pd]>[NH2:11][C@@H:12]([CH2:21][N:22]1[CH2:23][CH2:24][O:25][CH2:26][CH2:27]1)[C@H:13]([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[OH:14]

Participants

6

Reactant 3

HCID 6212ChloroformHCID 2723923Ammonium formateHCID 11531582(1S,2S)-2-Benzyloxycarbonylamino-3-morpholino-1-phenyl-1-propanol

Product 1

HCID 10513992(1S,2S)-2-amino-3-morpholino-1-phenyl-1-propanolYield 99%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalyst2×HCID 887MethanolSolvent2×

Procedure

(1S,2S)-2-Benzyloxycarbonylamino-3-morpholino-1-phenyl-1-propanol (3.82 g, 10.3 mmol) was dissolved in methanol (10 ml), ammonium formate (2.6 g, 41.3 mmol) and 10% palladium-carbon (888.5 mg, 8.09 mol %) were added thereto, and the mixture thus obtained was stirred overnight at room temperature. After confirming completion of the reaction with TLC (chloroform:methanol=9:1 and 7:3), palladium-carbon was removed by filtration and the resulting filtrate was concentrated to obtain the objective compound as a colorless oily material (2.34 g, yield: 99.0%).

Workup

  1. customthe mixture thus obtained
  2. customwas removed by filtration
  3. concentrationthe resulting filtrate was concentrated

Sources & evidence

ORD record
ord-67dd4fbd857f4fc6b5e6e5cd29ea8273
Source dataset
uspto-grants-1999_05
Patent number
US05907039

Linked notes

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