Water → 13-Methyl-16-(3,4,5-trimethoxy-benzylidene)-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-3,17-diol

HRID 1675923

Reaction equation

HRID 1675923 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:6]3[CH:14]([CH2:15][CH2:16][C:17]=2[CH:18]=1)[CH:13]1[C:9]([CH3:33])([C:10](=[O:32])[C:11](=[CH:19][C:20]2[CH:25]=[C:24]([O:26][CH3:27])[C:23]([O:28][CH3:29])=[C:22]([O:30][CH3:31])[CH:21]=2)[CH2:12]1)[CH2:8][CH2:7]3.[BH4-].[Na+].C(OCC)(=O)C.O>C1COCC1.CO>[CH3:33][C:9]12[CH2:8][CH2:7][CH:6]3[CH:14]([CH2:15][CH2:16][C:17]4[CH:18]=[C:2]([OH:1])[CH:3]=[CH:4][C:5]=43)[CH:13]1[CH2:12][C:11](=[CH:19][C:20]1[CH:21]=[C:22]([O:30][CH3:31])[C:23]([O:28][CH3:29])=[C:24]([O:26][CH3:27])[CH:25]=1)[CH:10]2[OH:32]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 4311764Sodium borohydrideHCID 50130353-Hydroxy-13-methyl-16-(3,4,5-trimethoxy-benzylidene)-6,7,8,9,11,12,13,14,15,16-decahydro-cyclopenta[a]phenanthren-17-one

Product 1

HCID 6734972913-Methyl-16-(3,4,5-trimethoxy-benzylidene)-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-3,17-diol

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A solution of 3-Hydroxy-13-methyl-16-(3,4,5-trimethoxy-benzylidene)-6,7,8,9,11,12,13,14,15,16-decahydro-cyclopenta[a]phenanthren-17-one (448 mg, 1.0 mmol, CAB01124) in THF/methanol (1:1, 40 ml) was cooled to 0° C. (ice bath) and sodium borohydride (100 mg, 2.64 mmol) was added. The reaction mixture was stirred for 2 h at this temperature, while it was turning from slightly yellow to colourless. The solution was transferred into a separation funnel and ethyl acetate (100 ml) and water (100 ml) were added. The organic layer was separated, washed with water (50 ml) and brine (50 ml), dried over sodium sulphate and concentrated under reduced pressure. Yield 445 mg (99%) white solid. 1H-NMR (CDCl3, 400 MHz), δ: 0.74 (s, 3H), 1.20-1.60 (m, 6H), 1.90-1.98 (m, 1H), 2.01-2.08 (m, 1H), 2.21-2.41 (m, 3H), 2.74-2.90 (m, 3H), 3.86 (s, 3H), 3.89 (s, 6H), 4.15 (d, J=9.4 Hz, 1H, H-17), 4.62 (s, 1H, —OH), 6.49-6.51 (m, 1H), 6.59 (d, J=2.3 Hz, 1H), 6.63-6.68 (m, 3H), 7.18 (d, J=8.2 Hz, 1H). LRMS (FAB+): 451.3 (100, [M+H]+).

Workup

  1. additionwas added
  2. customThe solution was transferred into a separation funnel
  3. customThe organic layer was separated
  4. washwashed with water (50 ml) and brine (50 ml)
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3c8387cc64ab4c5ca79129382766d3e7
Source dataset
uspto-grants-2011_08
Patent number
US08003783B2

Linked notes

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