Dimethylformamide → 54462-55-4

HRID 1779947Notes

Reaction equation

HRID 1779947 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 (3x), brine (1x), 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 (3x), brine (1x)
  3. dry with materialdried (sodium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-432d23c9ab694ca7b6b7194db90cc584
Source dataset
uspto-grants-1997_05
Patent number
US05629295

Reaction notes

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