Hydrochloric Acid → HCID 22862485, compound

HRID 1735150Notes

Reaction equation

HRID 1735150 reaction equation
[N+:1]([C:4]1[CH:31]=[CH:30][C:7]([O:8][C@H:9]2[CH2:14][CH2:13][C@H:12]3[C@H:15]4[C@H:25]([CH2:26][CH2:27][C@:10]23[CH3:11])[C@:23]2([CH3:24])[C@H:18]([N:19]([CH3:29])[C:20](=[O:28])[CH2:21][CH2:22]2)[CH2:17][CH2:16]4)=[CH:6][CH:5]=1)([O-])=O.[ClH:32]>CO.C(O)C.O=[Pt]=O>[ClH:32].[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([O:8][C@H:9]2[CH2:14][CH2:13][C@H:12]3[C@H:15]4[C@H:25]([CH2:26][CH2:27][C@:10]23[CH3:11])[C@:23]2([CH3:24])[C@H:18]([N:19]([CH3:29])[C:20](=[O:28])[CH2:21][CH2:22]2)[CH2:17][CH2:16]4)=[CH:30][CH:31]=1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 9802564HCID 9802564, compound

Product 1

HCID 22862485HCID 22862485, compound

Reagents, catalysts & solvents 3

HCID 345198Adams' catalystCatalystHCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

17β-(4-nitrophenoxy)-4-methyl-5α-4-azaandrostan-3-one (938 mg, 2.2 mmole) in MeOH (70 ml) was hydrogenated at 40 psi in the presence of PtO2 (400 mg) for 90 mins. To the resulting mixture was added 5% conc. HCl in absolute ethanol (4 ml) under N2, and then the mixture was filtered through a pad of celite. The filtrate was concentrated, vacuum dried, and then triturated with CH2Cl2 -hexane to give the title product, mp. 307°-310° C.

Workup

  1. filtrationthe mixture was filtered through a pad of celite
  2. concentrationThe filtrate was concentrated
  3. customvacuum dried
  4. customtriturated with CH2Cl2 -hexane

Sources & evidence

ORD record
ord-da2d6c9c4bc746cda34becd1139eafa1
Source dataset
uspto-grants-1996_07
Patent number
US05536727

Reaction notes

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