3alpha-Azido-5alpha-pregnan-20-one → 3alpha-Azido-21-bromo-5alpha-pregnan-20-one
Reaction equation
[N:1]([C@@H:4]1[CH2:23][CH2:22][C@@:21]2([CH3:24])[C@@H:6]([CH2:7][CH2:8][C@@H:9]3[C@@H:20]2[CH2:19][CH2:18][C@@:17]2([CH3:25])[C@H:10]3[CH2:11][CH2:12][C@@H:13]2[C:14](=[O:16])[CH3:15])[CH2:5]1)=[N+:2]=[N-:3].C1C=C[NH+]=CC=1.[Br:32][Br-]Br>C(O)C.C(Cl)(Cl)Cl.ClCCl>[N:1]([C@@H:4]1[CH2:23][CH2:22][C@@:21]2([CH3:24])[C@@H:6]([CH2:7][CH2:8][C@@H:9]3[C@@H:20]2[CH2:19][CH2:18][C@@:17]2([CH3:25])[C@H:10]3[CH2:11][CH2:12][C@@H:13]2[C:14](=[O:16])[CH2:15][Br:32])[CH2:5]1)=[N+:2]=[N-:3]Participants
5
Reactant 1
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 50 °C
Procedure
To a solution of 3α-azido-5α-pregnan-20-one (51.5 mg, 0.15 mmol) in absolute ethanol (3 mL) and chloroform (3 mL) was added pyridinium bromide perbromide (143 mg, 0.44 mmol) and the resulting mixture was heated at 50° C. for 45 min. Subsequently the mixture was diluted with dichloromethane and the organic layer was washed with water, brine and dried (Na2SO4). Evaporation of the solvent in vacuo and purification of the residue using flash column chromatography and petroleum ether/ethyl acetate 90/10 as elution solvent afforded the compound named above.
Workup
- washthe organic layer was washed with water, brine
- dry with materialdried (Na2SO4)
- customEvaporation of the solvent
- customin vacuo and purification of the residue
- washas elution solvent
- customafforded the compound
Sources & evidence
- ORD record
- ord-fd6b8733b58441ce9dbc3401d2248a21
- Source dataset
- uspto-grants-2006_06
- Patent number
- US07064116B2
Reaction notes
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