Ammonium Chloride → HCID 56609027, compound

HRID 1165744Notes

Reaction equation

HRID 1165744 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)CCCC)[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])[CH2:8][CH2:7]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][CH2:6][CH2:7][CH3:8])[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])[CH2:8][CH2:7]1

Participants

7

Reactant 3

HCID 25517Ammonium ChlorideHCID 56624790HCID 56624790, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 56609027HCID 56609027, compoundYield 124.3%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-30 °C

Procedure

At 0° C. under argon, 40 ml of a 5% solution of methyllithium in ether is added dropwise to a suspension of 9.3 g of copper(I) iodide in 186 ml of anhydrous tetrahydrofuran. The yellow solution is cooled to -30° C., and a solution of 7.4 g of 11β,17-dihydroxy-6α-methyl-21-valeryloxy-4-pregnene-3,20-dione in 186 ml of anhydrous tetrahydrofuran is added thereto. The mixture is agitated for 10 minutes at -25° C. and poured on 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 600 g of silica gel with a methylene chloride-acetone gradient (0-20% acetone), thus isolating 4.6 g of 11β,21-dihydroxy-6α-methyl-17-valeryloxy-4-pregnene-3,20-dione, mp 160° C.

Workup

  1. extractionAfter extraction with methylene chloride
  2. washthe organic solution is washed
  3. dry with materialdried over sodium sulfate
  4. customevaporated under vacuum
  5. customThe crude product is purified on 600 g of silica gel with a methylene chloride-acetone gradient (0-20% acetone)

Sources & evidence

ORD record
ord-160717fb25704390bf7ca2f23ea39ad2
Source dataset
uspto-grants-1990_03
Patent number
US04912098

Reaction notes

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