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

HRID 1765636Notes

Reaction equation

HRID 1765636 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([CH2:17][CH2:18][C:19](OC)=[O:20])[C:13](OC)=[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:20][CH2:19][CH2:18][CH2:17][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 86606597Dimethyl (2R)-2-{[(benzyloxy)carbonyl]amino}pentanedioate

Product 1

HCID 2757382(R)-Benzyl (1,5-dihydroxypentan-2-yl)carbamateYield 90%

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-4fc5996bb36244dc8c309fd9c4e8d29e
Source dataset
uspto-grants-2007_06
Patent number
US07226929B2

Reaction notes

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