Dimethylformamide → 54462-55-4

HRID 1941183Notes

Reaction equation

HRID 1941183 reaction equation
[Br-].[Li+].C(=O)([O-])[O-].[Li+].[Li+].CN(C)C=O.Br[C@@H:15]1[CH2:41][C@@:40]2([CH3:42])[C@@H:18]([CH2:19][CH2:20][C@@H:21]3[C@@H:39]2[CH2:38][CH2:37][C@@:36]2([CH3:43])[C@H:22]3[CH2:23][C@@H:24]3[O:29][C@@:28]4([O:35][CH2:34][C@H:32]([CH3:33])[CH2:31][CH2:30]4)[C@@H:26]([CH3:27])[C@@H:25]32)[CH2:17][C:16]1=[O:44]>C(OCC)(=O)C>[CH3:27][C@@H:26]1[C@:28]2([O:35][CH2:34][C@H:32]([CH3:33])[CH2:31][CH2:30]2)[O:29][C@H:24]2[CH2:23][C@@H:22]3[C@@:36]([CH3:43])([C@@H:25]12)[CH2:37][CH2:38][C@H:39]1[C@H:21]3[CH2:20][CH2:19][C@@H:18]2[C@:40]1([CH3:42])[CH:41]=[CH:15][C:16](=[O:44])[CH2:17]2

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11125Lithium CarbonateHCID 82050Lithium BromideHCID 54274457HCID 54274457, compound

Product 1

HCID 5384732154462-55-4Yield 98%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of lithium bromide (0.700 g, 8.06 mmol), lithium carbonate (1.20 g, 16.24 mmol) and anhydrous N,N-dimethylformamide (30 mL) were heated under nitrogen atmosphere to 95° C. To this mixture, (2α,5α,25R)-2-bromospirostan-3-one (4.00 g, 8.11 mmol) was added. The reaction mixture was stirred at 130° C. for 3 hours. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate, washed with water (3×), brine (1×), dried (sodium sulfate), filtered and concentrated in vacuo to afford 3.31 g, (98%) of the title compound.

Workup

  1. temperatureAfter cooling to room temperature
  2. washwashed with water (3×), brine (1×)
  3. dry with materialdried (sodium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ed4a92060a764d69bac069128be05a38
Source dataset
uspto-grants-1997_12
Patent number
US05703052

Reaction notes

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