HCID 22872549, compound → HCID 86750802, compound

HRID 1779921Notes

Reaction equation

HRID 1779921 reaction equation
Br[C@@H:2]1[C@@H:29]([OH:30])[C@@:28]2([CH3:31])[C@@H:13]([CH2:14][C@@H:15]3[O:20][C@@:19]4([O:26][CH2:25][C@H:23]([CH3:24])[CH2:22][CH:21]4[Br:27])[C@@H:17]([CH3:18])[C@@H:16]32)[C@H:12]2[C@H:3]1[C@:4]1([CH3:33])[C@@H:9]([CH2:10][CH2:11]2)[CH2:8][C@@H:7]([OH:32])[CH2:6][CH2:5]1.BrC1C[C@@H](C)CO[C@@]21[C@@H](C)[C@@H]1[C@]3(C)[C@@H](C[C@@H]1O2)[C@H]1[C@@H]([C@]2(C)[C@@H](CC1)C[C@@H](O)CC2)CC3=O>N1C=CC=CC=1.[Ag]=O>[Br:27][CH:21]1[CH2:22][C@@H:23]([CH3:24])[CH2:25][O:26][C@@:19]21[C@@H:17]([CH3:18])[C@@H:16]1[C@:28]3([CH3:31])[C@@H:13]([CH2:14][C@@H:15]1[O:20]2)[C@H:12]1[C@@H:3]([C@:4]2([CH3:33])[C@@H:9]([CH2:10][CH2:11]1)[CH2:8][C@@H:7]([OH:32])[CH2:6][CH2:5]2)[C@H:2]1[O:30][C@@H:29]31

Participants

5

Reactant 2

HCID 22872549HCID 22872549, compoundHCID 54041341HCID 54041341, compound

Product 1

HCID 86750802HCID 86750802, compound

Reagents, catalysts & solvents 2

HCID 92152Silver(II) oxideCatalystHCID 1049PyridineSolvent

Procedure

The following procedure is a variation of that described in Helv. Act. Chim., 1953, 36, 1241. ((3β,5α,11α,12β, 25R)-11,23-dibromospirostan-3,12-diol (18.08 g) was dissolved in pyridine (500 mL) at room temperature and treated with silver oxide (70.0 g). The resulting mixture was stirred in the dark for 71 hours. The mixture was filtered and the solid washed with ether and then chloroform. These washes were combined with the flitrate and concentrated. The resulting solid was purified by flash chromatography (1:1 hexane:ethyl acetate) to give 12.2 g of a 1:1 mixture of the title compound and (3β,5α,25R)-23-bromospirostan-3-ol-12-one. Further chromatography (7:3 hexane:ethyl acetate) provides pure title. compound.

Workup

  1. filtrationThe mixture was filtered
  2. washthe solid washed with ether
  3. concentrationconcentrated
  4. customThe resulting solid was purified by flash chromatography (1:1 hexane:ethyl acetate)
  5. customto give

Sources & evidence

ORD record
ord-a47c491e4a144b8fbf9201592ffef7f2
Source dataset
uspto-grants-1997_05
Patent number
US05629295

Reaction notes

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