N,N-Dimethylacrylamide → HCID 67301392, compound

HRID 1014970Notes

Reaction equation

HRID 1014970 reaction equation
[Si:1]([O:8][C@@H:9]1[C@@:28]2([CH3:29])[C:13](=[CH:14][CH:15]=[C:16]3[C@@H:27]2[CH2:26][CH2:25][C@@:24]2([CH3:30])[C@H:17]3[CH2:18][CH:19]=[C:20]2[C@H:21]([OH:23])[CH3:22])[CH2:12][C@@H:11]([O:31][Si:32]([C:35]([CH3:38])([CH3:37])[CH3:36])([CH3:34])[CH3:33])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH3:39][N:40]([CH3:45])[C:41](=[O:44])[CH:42]=[CH2:43].[H-].[Na+]>O1CCCC1>[Si:1]([O:8][C@@H:9]1[C@@:28]2([CH3:29])[C:13](=[CH:14][CH:15]=[C:16]3[C@@H:27]2[CH2:26][CH2:25][C@@:24]2([CH3:30])[C@H:17]3[CH2:18][CH:19]=[C:20]2[C@H:21]([O:23][CH2:43][CH2:42][C:41]([N:40]([CH3:45])[CH3:39])=[O:44])[CH3:22])[CH2:12][C@@H:11]([O:31][Si:32]([C:35]([CH3:37])([CH3:36])[CH3:38])([CH3:33])[CH3:34])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 17587N,N-DimethylacrylamideHCID 24758Sodium hydrideHCID 120200831alpha,3beta-bis(tert-butyldimethylsilyloxy)-20(R)-hydroxypregna-5,7,16-triene

Product 1

HCID 67301392HCID 67301392, compoundYield 93.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1α,3β-Bis(tert-butyldimethylsilyloxy)-20(R)-hydroxypregna-5,7,16-triene (316 mg, 0.57 mmol) was treated with N,N-dimethylacrylamide (175 mg, 1.77 mmol) and sodium hydride (60% in oil, 36 mg, 0.91 mmol) in tetrahydrofuran (5.7 ml) in the same manner as shown in Example 4(1) (at 0° C. for 1.5 hours and then at room temperature for 1.5 hours), followed by work up and purification using column chromatography (hexane:ethyl acetate=2:1) to give the titled compound (352 mg, 93.9%) as a colorless oil.

Workup

  1. customat 0° C.
  2. customfor 1.5 hours
  3. customup and purification

Sources & evidence

ORD record
ord-ad4237cbadc94e4893a83b74c843fb30
Source dataset
uspto-grants-2011_07
Patent number
US07985744B2

Reaction notes

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