Diethyl Ether → HCID 22875672, compound

HRID 2258014Notes

Reaction equation

HRID 2258014 reaction equation
[CH3:1][C@H:2]1[CH2:21][C@@H:20]2[C@:15]([CH3:23])([CH:16]=C[C:18](=O)[NH:19]2)[C@@H:14]2[C@@H:3]1[C@H:4]1[C@:11]([CH3:24])([CH2:12][CH2:13]2)[C@@H:7]([C:8](=[O:10])[CH3:9])[CH2:6][CH2:5]1.[CH3:25][Li].CI.[Cl-].[NH4+].CC[O:33][CH2:34][CH3:35]>O1CCCC1>[CH3:18][N:19]1[C:34](=[O:33])[CH:35]=[CH:16][C@@:15]2([CH3:23])[C@H:20]1[CH2:21][C@H:2]([CH3:1])[C@@H:3]1[C@@H:14]2[CH2:13][CH2:12][C@@:11]2([CH3:24])[C@H:4]1[CH2:5][CH2:6][C@@H:7]2[C:8]([CH3:25])([OH:10])[CH3:9]

Participants

7

Reactant 5

HCID 3283Diethyl EtherHCID 6328Methyl iodideHCID 25517Ammonium ChlorideHCID 22875684HCID 22875684, compoundHCID 178418348HCID 178418348, compound2×

Product 1

HCID 22875672HCID 22875672, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 73 mg (0.22 mmol) 7β-methyl-5α-4-azapregn-1-ene-3,20-dione in 7 ml dry tetrahydrofuran at -40° C. under N2 was added 3 eq methyllithium (0.7 mmol) in ether. The reaction was stirred and monitored by TLC. After three hours a second (0.5 eq) portion of methyllithium was added. After two hours 10 eq methyl iodide (2.2 mmol) was added and the reaction was allowed to warm to room temperature over 18 hrs. Aqueous ammonium chloride (5 ml) was added and the solvents were evaporated. The residue was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over magnesium sulfate, and evaporated. The product was purified via HPLC on a 19×300 mm 8 micron silica column using a 5 to 15% isopropanol/hexane gradient at 20 ml/min to yield 34 mg (0.095 mmol, 43% yield) of the title compound.

Workup

  1. customthe solvents were evaporated
  2. customThe residue was partitioned between ethyl acetate and water
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customThe product was purified via HPLC on a 19×300 mm 8 micron silica column

Sources & evidence

ORD record
ord-f2a1d4192c6848c48d506d75cb1f97a8
Source dataset
uspto-grants-1997_08
Patent number
US05658922

Reaction notes

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