Sodium borohydride → Boc-L-Homoser-Obzl

HRID 1353463Notes

Reaction equation

HRID 1353463 reaction equation
[BH4-].[Na+].[C:3]1([CH2:9][O:10][C:11](=[O:31])[C@@H:12]([NH:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:13][CH2:14][O:15]N2C(=O)CCC2=O)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>C1COCC1.O>[C:3]1([CH2:9][O:10][C:11](=[O:31])[C@@H:12]([NH:23][C:24]([O:26][C:27]([CH3:29])([CH3:28])[CH3:30])=[O:25])[CH2:13][CH2:14][OH:15])[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 58864167HCID 58864167, compound

Product 1

HCID 13970788Boc-L-Homoser-Obzl

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of NaBH4 (1.4 g, 37 mmol) in THF (80 mL) and H2O (20 mL) was added a solution of (2S)-2-[[(1,1-dimethylethoxy)carbonyl]amino]-4-[(2,5-dioxo-1-pyrrolidinyl)oxy]-butanoic acid phenylmethyl ester (10 g, 24 mmol) in THF at 0° C. After 15 min, the reaction mixture was quenched with NH4Cl (sat.), and extracted with EtOAc, dried over Na2SO4. Concentration in vacuo followed by flash chromatography (hexane-EtOAc, 7:3 to 6:4) afforded the product as colorless oil. LC-MS: 310 (M++1).

Workup

  1. customthe reaction mixture was quenched with NH4Cl (sat.)
  2. extractionextracted with EtOAc
  3. dry with materialdried over Na2SO4
  4. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-3a0042d022d649cd8f80987ca27d29b8
Source dataset
uspto-grants-2007_05
Patent number
US07220856B2

Reaction notes

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