Sodium borohydride → HCID 67349793, compound

HRID 1675924Notes

Reaction equation

HRID 1675924 reaction equation
[CH:1](=[C:8]1[C:24](=[O:25])[C:23]2([CH3:26])[CH:10]([CH:11]3[CH:20]([CH2:21][CH2:22]2)[C:19]2[CH:18]=[CH:17][C:16]([OH:27])=[CH:15][C:14]=2[CH2:13][CH2:12]3)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>C(O)C.C1COCC1>[CH:1](=[C:8]1[CH:24]([OH:25])[C:23]2([CH3:26])[CH:10]([CH:11]3[CH:20]([CH2:21][CH2:22]2)[C:19]2[CH:18]=[CH:17][C:16]([OH:27])=[CH:15][C:14]=2[CH2:13][CH2:12]3)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 67236326HCID 67236326, compound

Product 1

HCID 67349793HCID 67349793, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

16-Benzylidene-3-hydroxy-13-methyl-6,7,8,9,11,12,13,14,15,16-decahydro-cyclopenta[a]phenanthren-17-one (179 mg, 0.50 mmol, CAB01122) was dissolved in ethanol (10 ml) and THF (10 ml). The resulting light yellow solution was cooled to 0° C. (ice bath) and sodium borohydride (100 mg, 2.64 mmol) was added. The reaction mixture was stirred overnight at room temperature, the solvents were removed under reduced pressure and the residue was dissolved in ethyl acetate (40 ml). The organic solution was washed with water (2×25 ml) and brine (25 ml), dried over sodium sulphate and concentrated under reduced pressure. The residue was dissolved in a small amount of ethyl acetate and precipitated by addition of hexane. The white solid was filtered off and dried under high vacuum. Yield 175 mg (97%). 1H-NMR (d6-DMSO, 270 MHz), δ: 0.61 (s, 3H), 1.20-1.50 (m, 5H), 1.82-0.98 (m, 2H), 2.20-2.35 (m, 3H), 2.58-2.82 (m, 3H), 3.95-4.05 (m, 1H, H-17), 5.15 (d, J=6.2 Hz, 1H), 6.43 (s, 1H), 6.46 (d, J=2.3 Hz, 1H), 6.52 (dd, J=8.2, 2.3 Hz, 1H), 7.06 (d, J=8.2 Hz, 1H), 7.15-7.20 (m, 1H), 7.31-7.41 (m, 4H). LRMS (FAB+): 343.2 (80), 360.2 (100, [M]+). LRMS (FAB−): 359.3 (100, (M−H]−). HRMS (FAB+) 360.209709 C25H28O2 requires 360.208930

Workup

  1. additionwas added
  2. customthe solvents were removed under reduced pressure
  3. dissolutionthe residue was dissolved in ethyl acetate (40 ml)
  4. washThe organic solution was washed with water (2×25 ml) and brine (25 ml)
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated under reduced pressure
  7. dissolutionThe residue was dissolved in a small amount of ethyl acetate
  8. customprecipitated by addition of hexane
  9. filtrationThe white solid was filtered off
  10. customdried under high vacuum

Sources & evidence

ORD record
ord-b7d577e883d74d6281da0f113483d7e7
Source dataset
uspto-grants-2011_08
Patent number
US08003783B2

Reaction notes

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