HCID 18660097, compound → HCID 18660098, compound

HRID 1955998Notes

Reaction equation

HRID 1955998 reaction equation
[F:1][C:2]([F:37])([F:36])[C:3]1[CH:8]=[CH:7][C:6]([C:9]([F:12])([F:11])[F:10])=[CH:5][C:4]=1[NH:13][C:14]([C@H:16]1[CH2:21][CH2:20][C@H:19]2[C@H:22]3[C@H:32]([CH2:33][CH2:34][C@:17]12[CH3:18])[C@:30]1([CH3:31])[C:25]([O:26][C:27](=[O:35])[CH2:28][CH2:29]1)=[CH:24][CH2:23]3)=[O:15]>C1COCC1.[Rh]>[F:37][C:2]([F:1])([F:36])[C:3]1[CH:8]=[CH:7][C:6]([C:9]([F:12])([F:10])[F:11])=[CH:5][C:4]=1[NH:13][C:14]([C@H:16]1[CH2:21][CH2:20][C@H:19]2[C@H:22]3[C@H:32]([CH2:33][CH2:34][C@:17]12[CH3:18])[C@:30]1([CH3:31])[CH:25]([O:26][C:27](=[O:35])[CH2:28][CH2:29]1)[CH2:24][CH2:23]3)=[O:15]

Participants

4

Reactant 1

HCID 18660097HCID 18660097, compound

Product 1

HCID 18660098HCID 18660098, compound

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-(2',5'-bistrifluoromethylphenyl)-4-oxa-androst-5-en-3-one-17β-carboxamide (230 mg, 0.433 mml, prepared according to the procedures of Example 7) in THF (5 mL) was added 5% Rh/C (200 mg). After stirring the reaction mixture for overnight under hydrogen atmosphere, the reaction mixture was flushed with nitrogen, filtered, concentrated and purified by preparative tlc (50% EtOAc/hexane) to give pure product. Mass spec. M+ 532 (m+1, observed).

Workup

  1. customthe reaction mixture was flushed with nitrogen
  2. filtrationfiltered
  3. concentrationconcentrated
  4. custompurified by preparative tlc (50% EtOAc/hexane)
  5. customto give pure product

Sources & evidence

ORD record
ord-a450ac8c0cf64dcdaf22a22afb88d9c6
Source dataset
uspto-grants-1998_07
Patent number
US05777134

Reaction notes

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