Isopropanol → HCID 66960146, compound

HRID 1367748Notes

Reaction equation

HRID 1367748 reaction equation
C([O:8][C:9]1[C:10]([CH2:31][CH3:32])=[CH:11][C:12]2[CH:13]3[CH:21]([CH2:22][CH2:23][C:24]=2[CH:25]=1)[CH:20]1[C:16]([CH3:30])([C:17](=[CH:26][CH2:27][O:28][CH3:29])[CH2:18][CH2:19]1)[CH2:15][CH2:14]3)C1C=CC=CC=1.CC(O)C>C(O)(C)(C)C>[CH2:31]([C:10]1[C:9]([OH:8])=[CH:25][C:24]2[CH2:23][CH2:22][CH:21]3[CH:13]([CH2:14][CH2:15][C:16]4([CH3:30])[CH:20]3[CH2:19][CH2:18][C:17]4=[CH:26][CH2:27][O:28][CH3:29])[C:12]=2[CH:11]=1)[CH3:32]

Participants

4

Reactant 2

HCID 3776IsopropanolHCID 66959155HCID 66959155, compound

Product 1

HCID 66960146HCID 66960146, compound

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

A solution of 3-benzyloxy-2-ethyl-17-(2-methoxy-ethylidene)-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene (0.43 g, 1 mmol) in 50 ml tert-butanol was reflux and Na (0.46 g, 20 mmol) was added in small portions over a period of 6 hours. The mixture was refluxed for 18 h, cooled to room temperature and 2-propanol added to destroy excess sodium. The solvents were evaporated and the residual solid poured in water (20 ml). The organics were extracted with ethyl acetate and the organic layer was washed with water, brine, dried over MgSO4. The solvent was evaporated under vacuum. The crude oil was purified by chromatography (hexane/ethylacetate 15/1 to 8:1) to give 2-ethyl-17-(2-methoxy-ethylidene)-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-ol as a white powder, 230 mg (68%), mp=133-134° C.; 1H NMR (CDCl3, 270 MHz): 0.79 (s, 3H, CH3), 1.22 (t, J=7.4 Hz, 3H, CH3), 1.28-1.60 (m, 6H), 1.75-1.96 (m, 3H), 2.18 (m, 1H), 2.39 (m, 3H), 2.59 (q, J=7.4 Hz, 2H, CH2), 2.79 (m, 2H, H6), 3.35 (s, 3H, CH3O), 3.94 (m, 2H, CH2OMe), 5.11 (s, 1H, OH), 5.24 (m, 1H, CHCH2OH), 6.48 (s, 1H, ArH), 7.05 (s, 1H, ArH). 13C NMR (CDCl3, 400 MHz): 14.9 (CH3), 19.2, 23.5, 24.4, 26.7, 27.1, 28.1, 29.7, 36.4, 39.1, 44.4, 44.8, 53.5, 58.2, 70.2, 112.8, 115.7, 126.4, 127.5, 132.6, 135.5, 151.5, and 157.1. HPLC: 98%; HRMS (FAB+): found 340.24023 calcd. C23H32O2 340.24023.

Workup

  1. temperatureThe mixture was refluxed for 18 h
  2. customto destroy excess sodium
  3. customThe solvents were evaporated
  4. additionthe residual solid poured in water (20 ml)
  5. extractionThe organics were extracted with ethyl acetate
  6. washthe organic layer was washed with water, brine
  7. dry with materialdried over MgSO4
  8. customThe solvent was evaporated under vacuum
  9. customThe crude oil was purified by chromatography (hexane/ethylacetate 15/1 to 8:1)

Sources & evidence

ORD record
ord-b3d16cdd1caf48388b3ef5a399180df3
Source dataset
uspto-grants-2011_02
Patent number
US07893284B2

Reaction notes

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