Dimethylformamide → (8R,9S,13S,14S)-13-methyl-3-phenylmethoxy-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-one

HRID 1675908Notes

Reaction equation

HRID 1675908 reaction equation
[CH3:1][C:2]12[CH2:18][CH2:17][CH:16]3[CH:7]([CH2:8]CC4C=C(O)C=CC=43)[CH:6]1[CH2:5][CH:4]([CH2:20][C:21]1[CH:26]=[CH:25]N=[CH:23][CH:22]=1)[CH:3]2[OH:27].[C:28](=[O:31])([O-])[O-].[K+].[K+].C(Br)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.[CH3:42]N(C=O)C>>[CH3:1][C@@:2]12[C:3](=[O:27])[CH2:8][CH2:7][C@H:6]1[C@@H:5]1[CH2:4][CH2:20][C:21]3[CH:22]=[C:23]([O:31][CH2:28][C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)[CH:42]=[CH:25][C:26]=3[C@H:16]1[CH2:17][CH2:18]2

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 67348472HCID 67348472, compound

Product 1

HCID 11132151(8R,9S,13S,14S)-13-methyl-3-phenylmethoxy-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-oneYield 92%

Procedure

To a stirred solution of 2-ethyl estrone 1 (10.00 g, 33.5 mmol) in anhydrous DMF (100 ml) under inert atmosphere was added potassium carbonate (14.0 g, 100 mmol) followed by Benzyl bromide (4.78 ml, 40 mmol). The reaction was left to stir at r.t. over 2 days. The solid obtained was filtered using a Buchner funnel, dissolved in DCM, filtered to remove any inorganics and concentrated to obtain a white solid. The white solid obtained was re-crystallised with DCM:MeOH (90:10) to obtain the pure product the benzyl ether estrone derivative 2 (12.00 g, 92%) also as a white solid: 1H NMR (270 MHz, CDCl3) δ 0.90 (s, 3H, 18-CH3), 1.17-1.23 (t, J=7.4 Hz, CH2—CH3), 1.51-2.29 (m, 14H), 2.45-2.55 (m, 4H, 16-CH2), 2.62-2.70 (q, J=7.6 Hz, 2H, CH3—CH2), 2.84-2.90 (m, 2H, 6-CH2), 5.04 (s, 2H, CH2-phenyl) 6.64 (s, 4-H), 7.10 (s, 1-CH), 7.28-7.45 (m, 5H); FAB-HRMS calcd for C27H32O2 388.2357 found (M+) 388.2389.

Workup

  1. waitThe reaction was left
  2. customThe solid obtained
  3. filtrationwas filtered
  4. dissolutiondissolved in DCM
  5. filtrationfiltered
  6. customto remove any inorganics
  7. concentrationconcentrated
  8. customto obtain a white solid
  9. customThe white solid obtained
  10. customwas re-crystallised with DCM:MeOH (90:10)

Sources & evidence

ORD record
ord-ed785ddb652548349d5a8ddc4dcfd21e
Source dataset
uspto-grants-2011_08
Patent number
US08003783B2

Reaction notes

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