Lithium borohydride → (R)-Benzyl (1,5-dihydroxypentan-2-yl)carbamate

HRID 7286

Reaction equation

HRID 7286 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH:12]([CH2:16][CH2:17][C:18]([O-])=[O:19])[C:13]([O-])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Li+]>C1COCC1.[Cl-].[Na+].O.O>[OH:19][CH2:18][CH2:17][CH2:16][C@@H:12]([NH:11][C:9](=[O:10])[O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH2:13][OH:14]

Participants

6

Reactant 2

HCID 4148881Lithium borohydrideHCID 22017142[((Benzyloxy)carbonyl]amino}pentanedioate

Product 1

HCID 2757382(R)-Benzyl (1,5-dihydroxypentan-2-yl)carbamateYield 81.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of dimethyl (2R)-2-{[((benzyloxy)carbonyl]amino}pentanedioate (22.4 g) in dry THF (74 ml) was added dropwise over 1 h to a stirred mixture of lithium borohydride (4.5 g) in THF (200 ml) at room temperature, under nitrogen. Stirring at room temperature was continued for 3 days. The reaction mixture was diluted with brine and water, and extracted with ethyl acetate. The combined organic extracts were washed with brine, dried (over magnesium sulphate) and concentrated under reduced pressure to give the title compound (16.5 g) as a white solid.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried (over magnesium sulphate)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0716b8127315465ca5bb1dda1907bd78
Source dataset
uspto-grants-2006_08
Patent number
US07084139B2

Linked notes

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