Water → 3alpha-Hydroxy-21-(pyrid-3-yl)oxy-5beta-pregnan-20-one
Reaction equation
[OH:1][C@@H:2]1[CH2:22][CH2:21][C@@:20]2([CH3:23])[C@H:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:19]2[CH2:18][CH2:17][C@@:16]2([CH3:24])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C:12](=[O:15])[CH2:13]Br)[CH2:3]1.[OH:25][C:26]1[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=1.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[OH:1][C@@H:2]1[CH2:22][CH2:21][C@@:20]2([CH3:23])[C@H:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:19]2[CH2:18][CH2:17][C@@:16]2([CH3:24])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C:12](=[O:15])[CH2:13][O:25][C:26]2[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=2)[CH2:3]1Participants
6
Procedure
To a solution of 3α-hydroxy-21-bromo-5β-pregnan-20-one (300 mg, 0.76 mmol) in DMF (5 mL) was added 3-hydroxypyridine (215 mg, 2.27 mmol) and K2CO3 (313 mg, 2.27 mmol) and the mixture obtained was sired at 25° C. for 0.5 h. The reaction mixture was then poured into a separatory funnel containing water (30 mL) and the mixture was extracted with EtOAc (3×35 mL). The combined extracts were washed with water (2×25 mL) and then dried over Na2SO4. Removal of the solvent in vacuo resulted in the crude product which was purified by flash chromatography over silica gel to yield the pure 3α-hydroxy-21-(pyrid-3-yl)oxy-5β-pregnan-20-one (50 mg); mp 63-66° C.; TLC Rf (MeOH:CH2Cl2 5:95)=0.15.
Workup
- customthe mixture obtained
- additionThe reaction mixture was then poured into a separatory funnel
- extractionthe mixture was extracted with EtOAc (3×35 mL)
- washThe combined extracts were washed with water (2×25 mL)
- dry with materialdried over Na2SO4
- customRemoval of the solvent in vacuo
- customresulted in the crude product which
- customwas purified by flash chromatography over silica gel
Sources & evidence
- ORD record
- ord-90f8aa8092e14c6b9356fbcbb9a655d9
- Source dataset
- uspto-grants-2004_08
- Patent number
- US06780853B1
Reaction notes
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