Sodium hydride → HCID 86761363, compound

HRID 1014981Notes

Reaction equation

HRID 1014981 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][CH2:19][C@@H: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].[H-].[Na+].C1OCCOCCOCCOCCOC1.Br[CH2:57][C:58]([O:60][C:61]([CH3:64])([CH3:63])[CH3:62])=[O:59]>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][CH2:19][C@@H:20]2[C@@H:21]([O:23][CH2:57][C:58]([O:60][C:61]([CH3:64])([CH3:63])[CH3:62])=[O:59])[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

6

Reactant 4

HCID 24758Sodium hydrideHCID 3633615-Crown-5HCID 79177tert-Butyl bromoacetateHCID 11827838HCID 11827838, compound

Product 1

HCID 86761363HCID 86761363, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1α,3β-Bis(tert-butyldimethylsilyloxy)-20(S)-hydroxypregna-5,7-diene (150 mg, 0.267 mmol) was treated in tetrahydrofuran (2.7 ml) with sodium hydride (60% in oil, 65 mg, 1.625 mmol), 15-crown-5 (16 mg, 0.268 mmol) and tert-butyl bromoacetate (316 mg, 1.62 mmol) in the same manner as shown in Example 17(1) (heated at reflux for 17 hours), followed by work up and separation using preparative thin layer chromatography (0.5 mm×5 plates, hexane:ethyl acetate=5:1, developed once and then 0.5 mm×2 plates, hexane:ethyl acetate=7:1, developed twice) to give the titled compound (30 mg, 17%) as a colorless foam.

Workup

  1. temperatureas shown in Example 17(1) (heated at reflux for 17 hours)
  2. customseparation

Sources & evidence

ORD record
ord-e2d938372ac64c0db82f27a3b935fdc1
Source dataset
uspto-grants-2011_07
Patent number
US07985744B2

Reaction notes

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