Water → (R)-(+)-3-Benzyloxy-2-(Boc-amino)-1-propanol

HRID 2245394Notes

Reaction equation

HRID 2245394 reaction equation
[CH2:1]([O:8][CH2:9][C@@H:10]([C:19](ON1C(=O)CCC1=O)=[O:20])[NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].O>O1CCCC1>[CH2:1]([O:8][CH2:9][C@H:10]([NH:11][C:12](=[O:13])[O:14][C:15]([CH3:17])([CH3:16])[CH3:18])[CH2:19][OH:20])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 12879025Boc-Ser(Bzl)-OSu

Product 1

HCID 11065873(R)-(+)-3-Benzyloxy-2-(Boc-amino)-1-propanolYield 104.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under an atmosphere of argon, to a solution of 2,5-dioxopyrrolidin-1-yl O-benzyl-N-t-butoxycarbonyl-L-serinate (4.41 g) in tetrahydrofuran (30 mL) was added sodium borohydride (644 mg) in ice bath and the mixture was stirred at room temperature overnight. Water was added to the reaction solution, which was extracted with ethyl acetate. The organic layer was washed with an aqueous saturated ammonium chloride solution and brine, dried over anhydrous magnesium sulfate and concentrated to give the title compound (3.30 g) having the following physical data.

Workup

  1. extractionwas extracted with ethyl acetate
  2. washThe organic layer was washed with an aqueous saturated ammonium chloride solution and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-60f81027dff64ddb9ad92352addac1bb
Source dataset
uspto-grants-2010_03
Patent number
US07683094B2

Reaction notes

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