Methanesulfonic Acid → (2beta,3alpha,5alpha,17beta)-3-Hydroxy-2-(2,2-dimethyl-4-morpholinyl)androstane-17-carbonitrile methanesulfonate

HRID 233527Notes

Reaction equation

HRID 233527 reaction equation
[CH3:1][S:2]([OH:5])(=[O:4])=[O:3].[OH:6][C@@H:7]1[C@@H:24]([N:25]2[CH2:30][CH2:29][O:28][C:27]([CH3:32])([CH3:31])[CH2:26]2)[CH2:23][C@@:22]2([CH3:33])[C@@H:9]([CH2:10][CH2:11][C@@H:12]3[C@@H:21]2[CH2:20][CH2:19][C@@:17]2([CH3:18])[C@H:13]3[CH2:14][CH2:15][C@@H:16]2[C:34]#[N:35])[CH2:8]1>C(O)C>[CH3:1][S:2]([OH:5])(=[O:4])=[O:3].[OH:6][C@@H:7]1[C@@H:24]([N:25]2[CH2:30][CH2:29][O:28][C:27]([CH3:31])([CH3:32])[CH2:26]2)[CH2:23][C@@:22]2([CH3:33])[C@@H:9]([CH2:10][CH2:11][C@@H:12]3[C@@H:21]2[CH2:20][CH2:19][C@@:17]2([CH3:18])[C@H:13]3[CH2:14][CH2:15][C@@H:16]2[C:34]#[N:35])[CH2:8]1

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 54130454(2beta,3alpha,5alpha,17beta)-3-Hydroxy-2-(2,2-dimethyl-4-morpholinyl)androstane-17-carbonitrile

Product 1

HCID 86750184(2beta,3alpha,5alpha,17beta)-3-Hydroxy-2-(2,2-dimethyl-4-morpholinyl)androstane-17-carbonitrile methanesulfonate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of methanesulfonic acid (186 mg) in ethanol (2 ml) was added to a suspension of (2β,3α,5α,17β)-3-hydroxy-2-(2,2-dimethyl-4-morpholinyl)androstane-17-carbonitrile (800 mg) in ethanol (8 ml) and the mixture was stirred for 5 min. Removal of the solvent under reduced pressure afforded a solid which was precipitated from ethanol-diethyl ether to give (2β,3α,5α,17β)-3-hydroxy-2-(2,2-dimethyl-4-morpholinyl)androstane-17-carbonitrile methanesulfonate (1:1) salt (890 mg). [α]D +100.2° (c 0.2).

Workup

  1. customRemoval of the solvent under reduced pressure
  2. customafforded a solid which
  3. customwas precipitated from ethanol-diethyl ether

Sources & evidence

ORD record
ord-15dadd39773e4674bd30fe12470f8472
Source dataset
uspto-grants-1997_01
Patent number
US05593983

Reaction notes

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