(7alpha,17beta)-3-Methoxy-7-methylestr-1,3,5(10),14-tetraen-17-ol → (7alpha,14beta,17beta)-3-Methoxy-7-methylestr-1,3,5(10)-trien-17-ol

HRID 1815778Notes

Reaction equation

HRID 1815778 reaction equation
[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:18]2[C@@H:17]3[C@H:8]([C:9]4[C@@:13]([CH2:15][CH2:16]3)([CH3:14])[C@@H:12]([OH:21])[CH2:11][CH:10]=4)[C@H:7]([CH3:22])[CH2:6][C:5]=2[CH:4]=1>[Pd].C(O)C.ClCCl>[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:18]2[C@@H:17]3[C@H:8]([C@@H:9]4[C@@:13]([CH2:15][CH2:16]3)([CH3:14])[C@@H:12]([OH:21])[CH2:11][CH2:10]4)[C@H:7]([CH3:22])[CH2:6][C:5]=2[CH:4]=1

Participants

5

Reactant 1

HCID 69624986(7alpha,17beta)-3-Methoxy-7-methylestr-1,3,5(10),14-tetraen-17-ol

Product 1

HCID 69788873(7alpha,14beta,17beta)-3-Methoxy-7-methylestr-1,3,5(10)-trien-17-olYield 95.6%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

i)—A mixture of (7α,17β)-3-methoxy-7-methylestr-1,3,5(10),14-tetraen-17-ol [Segaloff, et al, Steroids 22, 99 (1973); 86.2 g] and palladium on activated carbon (5%; 34.5 g) in ethanol (578 ml) and dichloromethane (414 ml) was stirred under hydrogen (3 bar) at room temperature for 24 h. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure, to give (7α,14β,17β)-3-methoxy-7-methylestr-1,3,5(10)-trien-17-ol (83.0 g). The product was used in the following step without further purification.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-52912f247795484bbb659b59d6a2f3db
Source dataset
uspto-grants-2005_04
Patent number
US06881728B1

Reaction notes

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