Sodium borohydride → HCID 67490796, compound

HRID 1917434Notes

Reaction equation

HRID 1917434 reaction equation
[C:1]([O:5][C:6]([C@@:8]12[CH2:24][O:23][CH:22]([OH:25])[CH:9]1[C:10](=[O:21])[N:11]([C@@H:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH3:14])[CH2:12]2)=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>O1CCCC1.C(O)C>[C:1]([O:5][C:6]([C@@:8]1([CH2:24][OH:23])[CH:9]([CH2:22][OH:25])[C:10](=[O:21])[N:11]([C@@H:13]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH3:14])[CH2:12]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 67491032HCID 67491032, compound

Product 1

HCID 67490796HCID 67490796, compoundYield 43.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a cooled solution (−20° C.) of (3aS)-1-hydroxy-6-oxo-5-[(R)-1-phenylethyl]tetrahydrofuro[3,4-c]pyrrole-3a-carboxylic acid tert-butyl ester (350 mg, 1.01 mmol) in tetrahydrofuran and ethanol (10 mL; 4:1), sodium borohydride (38.0 mg, 1.00 mmol) was added portionwise, and the mixture was stirred at the same temperature for 5.5 h. The reaction mixture was concentrated in vacuo and taken up in AcOEt and water. The layers were separated and the aqueous layer extracted with AcOEt. The combined extracts were washed with brine, dried (Na2SO4), and concentrated in vacuo. The residue was purified by silica gel chromatography eluting with 90% AcOEt in hexane to afford the title compound (153 mg) as a colorless oil.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customThe layers were separated
  3. extractionthe aqueous layer extracted with AcOEt
  4. washThe combined extracts were washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel chromatography
  8. washeluting with 90% AcOEt in hexane

Sources & evidence

ORD record
ord-02607f0535c34aef85b1c35b697a63ec
Source dataset
uspto-grants-2013_12
Patent number
US08618094B2

Reaction notes

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