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Methanesulfonic Acid → (2beta,3alpha,5alpha)-3-Hydroxy-2-(2,2-dimethyl-4-morpholinyl)-21-thiocyanatopregnane-11,20-dione

HRID 233520
Notes
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Reaction equation

HRID 233520 reaction equation
Cl[CH2:2][C:3](=[O:33])[C@@H:4]1[C@:21]2([CH3:22])[C@H:7]([C@H:8]3[C@H:18]([C:19](=[O:23])[CH2:20]2)[C@:16]2([CH3:17])[C@H:11]([CH2:12][C@H:13]([OH:32])[C@@H:14]([N:24]4[CH2:29][CH2:28][O:27][C:26]([CH3:31])([CH3:30])[CH2:25]4)[CH2:15]2)[CH2:10][CH2:9]3)[CH2:6][CH2:5]1.CS(O)(=O)=O.[S-:39][C:40]#[N:41].[K+].C(=O)([O-])[O-].[Na+].[Na+]>CO.O>[OH:32][C@@H:13]1[C@@H:14]([N:24]2[CH2:29][CH2:28][O:27][C:26]([CH3:31])([CH3:30])[CH2:25]2)[CH2:15][C@@:16]2([CH3:17])[C@@H:11]([CH2:10][CH2:9][C@@H:8]3[C@@H:18]2[C:19](=[O:23])[CH2:20][C@@:21]2([CH3:22])[C@H:7]3[CH2:6][CH2:5][C@@H:4]2[C:3](=[O:33])[CH2:2][S:39][C:40]#[N:41])[CH2:12]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 6395Methanesulfonic AcidHCID 10340Sodium CarbonateHCID 516872Potassium thiocyanateHCID 10672358(2beta,3alpha,5alpha)-21-Chloro-3-hydroxy-2-(2,2-dimethyl-4-morpholinyl)pregnane-11,20-dione

Product 1

HCID 10696819(2beta,3alpha,5alpha)-3-Hydroxy-2-(2,2-dimethyl-4-morpholinyl)-21-thiocyanatopregnane-11,20-dione
Yield 17.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

To (2β,3α,5α)-21-chloro-3-hydroxy-2-(2,2-dimethyl-4-morpholinyl)pregnane-11,20-dione (3.1 g) was added a solution of methanesulfonic acid (615 mg) in methanol (63 ml) and then a solution of potassium thiocyanate (12.4 g) in water (32 ml). The resulting solution was stirred at room temperature for 24 h, poured into water and sodium carbonate was then added until the pH exceeded 9. The precipitated solid was filtered off, washed with water and dissolved in dichloromethane. This solution was dried over sodium sulfate and the solvent was removed under reduced pressure. The residue was chromatographed on silica gel and the purified product was crystallised from diethyl ether and then from methanol to give (2β,3α,5α)-3-hydroxy-2-(2,2-dimethyl-4-morpholinyl)-21-thiocyanatopregnane-11,20-dione (572 mg). m.p. 197°-198° C.; [α]D +99.3° (c 0.8).

Workup

  1. additionwas then added until the pH
  2. filtrationThe precipitated solid was filtered off
  3. washwashed with water
  4. dissolutiondissolved in dichloromethane
  5. dry with materialThis solution was dried over sodium sulfate
  6. customthe solvent was removed under reduced pressure
  7. customThe residue was chromatographed on silica gel
  8. customthe purified product was crystallised from diethyl ether

Sources & evidence

ORD record
ord-27159a280d9542989db8091d57903fca
Source dataset
uspto-grants-1997_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05593983

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes