Ammonium Chloride → HCID 13131725, compound

HRID 279829Notes

Reaction equation

C[Li].[OH:3][C@H:4]1[CH2:30][C@@:29]2([CH3:31])[C@@H:15]([CH2:16][CH2:17][C@:18]2([OH:32])[C:19](=[O:28])[CH2:20][O:21]C(=O)CC(C)C)[C@H:14]2[C@H:5]1[C@:6]1([CH3:35])[C:11]([C@@H:12]([CH3:33])[CH2:13]2)=[CH:10][C:9](=[O:34])[CH:8]=[CH:7]1.[Cl-].[NH4+]>CCOCC.O1CCCC1.[Cu]I>[OH:3][C@H:4]1[CH2:30][C@@:29]2([CH3:31])[C@@H:15]([CH2:16][CH2:17][C@:18]2([O:32][C:4](=[O:3])[CH2:5][CH:6]([CH3:11])[CH3:7])[C:19](=[O:28])[CH2:20][OH:21])[C@H:14]2[C@H:5]1[C@:6]1([CH3:35])[C:11]([C@@H:12]([CH3:33])[CH2:13]2)=[CH:10][C:9](=[O:34])[CH:8]=[CH:7]1

Participants

Conditions

Temperature: -30 °C

Procedure

Under argon at 0° C., 200 ml of a 5% solution of methyllithium in ether is added dropwise to a suspension of 36.5 g of copper(I) iodide in 730 ml of anhydrous tetrahydrofuran. The yellow solution is cooled to -30° C., and a solution of 29.0 g of 11β,17-dihydroxy-21-isovaleryloxy-6α-methyl-1,4-pregnadiene-3,20-dione in 730 ml of anhydrous tetrahydrofuran is added thereto. The mixture is stirred further for 10 minutes at -25° C. and poured onto an aqueous ammonium chloride solution. After extraction with methylene chloride, the organic solution is washed, dried over sodium sulfate, and evaporated under vacuum. The crude product is purified on 750 g of silica gel with a methylene chloride-acetone gradient (0-20% acetone), yielding 18.2 g of 11β,21-dihydroxy-17-isovaleryloxy-6α-methyl-1,4-pregnadiene-3,20-dione, mp 164° C.

Workup

extractionAfter extraction with methylene chloride
washthe organic solution is washed
dry with materialdried over sodium sulfate
customevaporated under vacuum
customThe crude product is purified on 750 g of silica gel with a methylene chloride-acetone gradient (0-20% acetone)

Sources & evidence

ORD record: ord-032beb7b537541ada97552650239afea
Source dataset: uspto-grants-1986_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04587236

Reaction notes

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