N,N-Dimethylacrylamide → HCID 69630616, compound

HRID 1792223Notes

Reaction equation

HRID 1792223 reaction equation
[Si:1]([O:8][C@@H:9]1[C@@:26]2([CH3:27])[C:13](=[CH:14][CH2:15][C@@H:16]3[C@@H:25]2[CH2:24][CH2:23][C@@:21]2([CH3:22])[C@H:17]3[CH2:18][CH2:19][C@@H:20]2[CH2:28][OH:29])[CH2:12][CH:11]([O:30][Si:31]([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:33])[CH3:32])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH3:38][N:39]([CH3:44])[C:40](=[O:43])[CH:41]=[CH2:42].[H-].[Na+].C1OCCOCCOCCOCCOC1.[Cl-].[NH4+]>O1CCCC1>[Si:1]([O:8][C@@H:9]1[C@@:26]2([CH3:27])[C:13](=[CH:14][CH2:15][C@@H:16]3[C@@H:25]2[CH2:24][CH2:23][C@@:21]2([CH3:22])[C@H:17]3[CH2:18][CH2:19][C@@H:20]2[CH2:28][O:29][CH2:42][CH2:41][C:40]([N:39]([CH3:44])[CH3:38])=[O:43])[CH2:12][C@@H:11]([O:30][Si:31]([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:32])[CH3:33])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

7

Reactant 5

HCID 17587N,N-DimethylacrylamideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 3633615-Crown-5HCID 69630567HCID 69630567, compound

Product 1

HCID 69630616HCID 69630616, compoundYield 60.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 1α,3-bis(tert-butyldimethylsilyloxy)-17β-(hydroxymethyl)androst-5-ene (18.4 g), was added N,N-dimethylacrylamide (9.95 g), sodium hydride (60% in oil, 2.0 g), 15-crown-5 (2.2 g) and tetrahydrofuran (73.5 ml), followed by reaction at 0° C. for 8 hours. After stopping the reaction by adding a saturated aqueous ammonium chloride solution, the organic layer was washed with a saturated aqueous sodium bicarbonate solution and saturated brine, dried over anhydrous magnesium sulfate and evaporated under reduced pressure to remove the solvent. The resulting residue was mixed with methanol (90 ml), stirred at room temperature while under suspension, followed by centrifugation. The thus obtained solid was dried to give the titled compound (13.2 g).

Workup

  1. customfollowed by reaction at 0° C. for 8 hours
  2. customthe reaction
  3. washthe organic layer was washed with a saturated aqueous sodium bicarbonate solution and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated under reduced pressure
  6. customto remove the solvent
  7. additionThe resulting residue was mixed with methanol (90 ml)
  8. customThe thus obtained solid was dried

Sources & evidence

ORD record
ord-4b555da856334d37b2959f11092ad220
Source dataset
uspto-grants-2006_07
Patent number
US07074777B2

Reaction notes

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