Sodium borohydride → HCID 9858020, compound

HRID 7871Notes

Reaction equation

HRID 7871 reaction equation
[CH2:1]([C:5]12[CH2:17][CH:16]([CH2:18][CH:19]=[O:20])[C:15](=[O:21])[C:14]([CH3:22])=[C:13]1[C:12]1[C:7](=[CH:8][C:9]([OH:23])=[CH:10][CH:11]=1)[CH2:6]2)[CH2:2][CH2:3][CH3:4].[BH4-].[Na+]>CC(O)C>[CH2:1]([C:5]12[CH2:17][CH:16]([CH2:18][CH2:19][OH:20])[C:15](=[O:21])[C:14]([CH3:22])=[C:13]1[C:12]1[C:7](=[CH:8][C:9]([OH:23])=[CH:10][CH:11]=1)[CH2:6]2)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86587280HCID 86587280, compound

Product 1

HCID 9858020HCID 9858020, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of (2RS,9aSR)-9a-butyl-7-hydroxy-4-methyl-2-(2-oxo-ethyl)-1,2,9,9a-tetrahydro-3H-fluoren-3-one (17 mg, 0.05 mmol) in 2-propanol (2 mL) was treated with NaBH4 (1.9 mg, 0.05 mmol) and the mixture was stirred at room temperature for 40 minutes. The solvent was evaporated under vacuum. The residue was taken up in EtOAc (60 mL), washed with 0.2N HCl (30 mL), 5% NaHCO3, and brine, dried over MgSO4, filtered, and concentrated under vacuum to a gum (24 mg). This material was purified by PLC on a 0.1×20×20 cm silica gel GF plate using 2:1 hexanes-EtOAc as developing solvent. The UV visible band at Rf 0.06-0.11 afforded (2RS,9aSR)-9a-butyl-7-hydroxy-2-(2-hydroxyethyl)-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one as an oil.

Workup

  1. customThe solvent was evaporated under vacuum
  2. washwashed with 0.2N HCl (30 mL), 5% NaHCO3, and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum to a gum (24 mg)
  6. customThis material was purified by PLC on a 0.1×20×20 cm silica gel GF plate

Sources & evidence

ORD record
ord-6d0e5e3c98d34755babed58fc6c14987
Source dataset
uspto-grants-2006_08
Patent number
US07087599B2

Reaction notes

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