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Hydrochloric Acid → 16beta-Methly-5-androsten-17-one

HRID 861642
Notes
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Reaction equation

HRID 861642 reaction equation
C(O[C@H:5]1[CH2:22][CH2:21][C@@:20]2([CH3:23])[C:7](=[CH:8][CH2:9][C@@H:10]3[C@@H:19]2[CH2:18][CH2:17][C@@:15]2([CH3:16])[C@H:11]3[CH2:12][C:13]([CH3:28])=[C:14]2NC(=O)C)[CH2:6]1)(=O)C.[OH2:29].Cl.C(CC(C)(C)C)(C)C.C(OCC)(=O)C>C1COCC1>[CH3:28][C@H:13]1[CH2:12][C@H:11]2[C@H:10]3[C@H:19]([CH2:18][CH2:17][C@:15]2([CH3:16])[C:14]1=[O:29])[C@:20]1([CH3:23])[C:7]([CH2:6][CH2:5][CH2:22][CH2:21]1)=[CH:8][CH2:9]3
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 18516502EtOAc isooctaneHCID 5662530017-Acetamido-16-methyl-5,16-androstadien-3beta-ol acetate

Product 1

HCID 5434781216beta-Methly-5-androsten-17-one

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Procedure

The crude methyl enamide acetate (3, 1.94 g) was refluxed in 100 ml each of THF and water with 10 ml of concentrated HCl for 31/2 hours. Following the usual work-up the crude hydroxy methyl ketones (5 and 6) were converted to the 3-acetates. Silica gel thin layer chromotography using isooctane-ethyl acetate (21:4) roughly showed a 3:1 mixture of polar (Rf 0.17) and mobile (Rf 0.21) products, representing a mixture of the 16α-methyl and 16β-methyl-17-ones, respectively. Crystallization of the original 3-hydroxy mixture gave 425 mg of pure 16β-methyl-5-androsten-17-one (6), mp 168°-170°. The mother liquor residue (660 mg) represented a mixture of 16α and 16β-methyl-3-hydroxy-17-ones (5 and 6).

Workup

  1. custom2 hours
  2. additiona 3:1 mixture of polar (Rf 0.17) and mobile (Rf 0.21) products
  3. customCrystallization of the original 3-hydroxy mixture

Sources & evidence

ORD record
ord-69193ef4deca4fa492c5e1c238e4f8bd
Source dataset
uspto-grants-1998_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05714481

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes