Tetrahydrofuran → tert-butyl N-[(2S)-1-oxo-3-phenylpropan-2-yl]carbamate

HRID 573008

Reaction equation

HRID 573008 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:17](N(OC)C)=[O:18])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].C1COCC1.S([O-])(O)(=O)=O.[K+]>CC1CCCO1.O>[C:1]([O:5][C:6](=[O:7])[NH:8][C@@H:9]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH:17]=[O:18])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 516920Potassium bisulfateHCID 110559451,1-Dimethylethyl N-((1S)-2-(methoxymethylamino)-2-oxo-1-(phenylmethyl)ethyl)carbamateHCID 21226445Aluminium lithium hydride

Product 1

HCID 6998013tert-butyl N-[(2S)-1-oxo-3-phenylpropan-2-yl]carbamate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 73012-MethyltetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

1090 mg (3.5 mmol) Nα-(tert-butoxycarbonyl)-N-methoxy-N-methyl-L-phenylalanine-amide was dissolved in 20 mL 2-methyltetrahydrofuran and cooled to 0° C. Then 4.2 mL (4.2 mmol) of a 1M lithium aluminum hydride solution was added slowly to THF, and the reaction mixture was stirred for 30 min at 0° C. Next 5% aqueous potassium hydrogen sulfate solution was added cautiously. The batch was then diluted with water and extracted with MTBE. The organic phase was dried over magnesium sulfate and concentrated in vacuo, yielding 820 mg (94% of the theoretical) of the title compound.

Workup

  1. extractionextracted with MTBE
  2. dry with materialThe organic phase was dried over magnesium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f81bbe8e7a53400187c1f199d5bbf0ab
Source dataset
uspto-grants-2015_05
Patent number
US09029406B2

Linked notes

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