Hydrochloric Acid → HCID 22884996, compound

HRID 1599481Notes

Reaction equation

HRID 1599481 reaction equation
[CH3:1][N:2]1[C:19]2[C@:14]([CH3:21])([CH2:15][CH2:16][C:17](=[O:20])[CH:18]=2)[C@@H:13]2[C@H:4]([C@H:5]3[C@@:9]([CH2:11][CH2:12]2)([CH3:10])[CH2:8][C:7](=[O:22])[CH2:6]3)[CH2:3]1.N#N.[H-].C(O[Al](OC(C)(C)C)OC(C)(C)C)(C)(C)C.[Li+].Cl>C1COCC1>[OH:22][C@H:7]1[CH2:6][C@H:5]2[C@H:4]3[C@H:13]([CH2:12][CH2:11][C@:9]2([CH3:10])[CH2:8]1)[C@:14]1([CH3:21])[C:19](=[CH:18][C:17](=[O:20])[CH2:16][CH2:15]1)[N:2]([CH3:1])[CH2:3]3

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 947NitrogenHCID 16710494Lithium tri-tert-butoxyaluminohydrideHCID 53819571HCID 53819571, compound

Product 1

HCID 22884996HCID 22884996, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 6-methyl-6-azaandrost-4-ene-3,16-dione (13, R2 =H) (273 mg, 0.906 mmoles) in THF (15 mL) at 0° C. in a N2 atmosphere was added lithium tri-tertbutoxyaluminum hydride (1.0M/THF) (2.36 mL, 2.6 mmoles) and the mixture stirred at 0° C. for 24 hours. The pH was brought to 4 with 0.5M HCl, and the mixture evaporated in vacuo. The residue was dissolved in methylene chloride and washed with H2O and brine and dried over MgSO4. Evaporation in vacuo and flash chromatography on silica gel with 4% methanol in methylene chloride gave (14, R2 =H) as a white solid. NMR (CDCl3): δ 1.03 (s, 3H, 18-Me); 1.29 (s, 3H, 19-Me); 2.87 (s, 3H, N-CH3); 4.46 (m, 1H, 16-H); 5.32 (s, 1H, 4-H).

Workup

  1. customthe mixture evaporated in vacuo
  2. dissolutionThe residue was dissolved in methylene chloride
  3. washwashed with H2O and brine
  4. dry with materialdried over MgSO4
  5. customEvaporation in vacuo and flash chromatography on silica gel with 4% methanol in methylene chloride
  6. customgave (14, R2 =H) as a white solid

Sources & evidence

ORD record
ord-6a6b7a03bf4f45c781bde1ad220b3241
Source dataset
uspto-grants-1998_04
Patent number
US05741795

Reaction notes

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