Borane;tetrahydrofuran → tert-butyl (3R)-3-(9H-fluoren-9-ylmethoxycarbonylamino)-4-hydroxy-butanoate

HRID 333878Notes

Reaction equation

HRID 333878 reaction equation
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([NH:18][C@H:19]([CH2:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C:20](O)=[O:21])=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.B.C1COCC1>O1CCCC1>[CH:10]1[C:11]2[CH:12]([CH2:14][O:15][C:16]([NH:18][C@@H:19]([CH2:20][OH:21])[CH2:23][C:24]([O:26][C:27]([CH3:28])([CH3:30])[CH3:29])=[O:25])=[O:17])[C:13]3[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=3)[C:6]=2[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 70188164-tert-Butyl N-((9H-Fluoren-9-ylmethoxy)carbonyl)-D-aspartate

Product 1

HCID 56845319tert-butyl (3R)-3-(9H-fluoren-9-ylmethoxycarbonylamino)-4-hydroxy-butanoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(R)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-4-tert-butoxy-4-oxobutanoic acid (8.2 g) in tetrahydrofuran (2 mL) was treated with BH3-THF (39.9 mL) overnight. The reaction mixture was quenched with water and extracted with dichloromethane. The combined organic layer was washed with brine, dried over MgSO4, filtered and concentrated. The residue was purified by flash chromatography, eluting with 30% ethyl acetate in petroleum ether, to provide the title compound.

Workup

  1. customThe reaction mixture was quenched with water
  2. extractionextracted with dichloromethane
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography
  8. washeluting with 30% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-7639a5feaac940abbc624a3a74c28343
Source dataset
uspto-grants-2014_11
Patent number
US08883784B2

Reaction notes

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