HCID 10578596, compound → HCID 386444, compound

HRID 1004853Notes

Reaction equation

HRID 1004853 reaction equation
[F:1][C:2]([F:40])([F:39])[CH2:3][O:4][C:5]1[C:6]([O:31]CC2C=CC=CC=2)=[CH:7][C:8]2[CH2:9][CH2:10][C@@H:11]3[C@@H:20]([C:21]=2[CH:22]=1)[CH2:19][CH2:18][C@@:16]1([CH3:17])[C@H:12]3[CH2:13][CH2:14][C@@H:15]1[O:23]CC1C=CC=CC=1>C1COCC1.[OH-].[OH-].[Pd+2]>[F:1][C:2]([F:39])([F:40])[CH2:3][O:4][C:5]1[C:6]([OH:31])=[CH:7][C:8]2[CH2:9][CH2:10][C@@H:11]3[C@@H:20]([C:21]=2[CH:22]=1)[CH2:19][CH2:18][C@@:16]1([CH3:17])[C@H:12]3[CH2:13][CH2:14][C@@H:15]1[OH:23]

Participants

4

Reactant 1

HCID 10578596HCID 10578596, compound

Product 1

HCID 386444HCID 386444, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Pd(OH)2 --C(20%, 1.0 g) was added carefully under argon atmosphere to a solution of estradiol (7) (1.0 g, 1.8 mmol) in anhydrous THF (50 mL). The resulting mixture was hydrogenated at 45-50 psi on a Parr apparatus for 24 h. The catalyst was removed by filtration using a celite pad under argon atmosphere, and the pad was washed with dichloromethane (200 mL). Evaporation of the filtrate under reduced pressure, followed by purification on a silica gel column, gave compound (9) (0.5 g, 75%): mp 167-168° C.; IR (KBr) 3550, 2960-2840, 1590, 1510, 870 cm-1 ; 1H NMR (CDCl)3 δ 0.80 (s, 3H), 1.10-2.40 (m, 13H), 2.70-2.85 (m, 2H), 3.75 (m, 1H), 4.40 (q, J=8.5 Hz, 2H), 5.35 (s, 1H, OH), 5.5 (s, 1H), 6.70 (s, 1H), 6.80 (s, 1H); MS m/z (relative intensity) 370 (100), 311 (9), 270 (8), 244 (8), 205(6). Anal. (C20H25O3 0.7 H2O) C, H.

Workup

  1. customThe catalyst was removed by filtration
  2. washthe pad was washed with dichloromethane (200 mL)
  3. customEvaporation of the filtrate under reduced pressure
  4. customfollowed by purification on a silica gel column

Sources & evidence

ORD record
ord-5cfa3b443afa49a0a62ffab89b909314
Source dataset
uspto-grants-2000_04
Patent number
US06051726

Reaction notes

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