Methylamine → HCID 12961946, compound

HRID 1065689Notes

Reaction equation

HRID 1065689 reaction equation
[C:1]([OH:4])(=[O:3])[CH3:2].C(O)(=O)C.O[C@H:10]1[CH2:27][CH2:26][C@@:25]2([CH3:28])[C@@H:12]([CH2:13][CH2:14][C@@H:15]3[C@@H:24]2[CH2:23][CH2:22][C@@:20]2([CH3:21])[C@H:16]3[CH2:17][C@@H:18]([OH:30])[C:19]2=O)[CH2:11]1.[CH3:31][NH2:32]>C(O)C>[C:1]([O:4][C@H:10]1[CH2:27][CH2:26][C@@:25]2([CH3:28])[C@@H:12]([CH2:13][CH2:14][C@@H:15]3[C@@H:24]2[CH2:23][CH2:22][C@@:20]2([CH3:21])[C@H:16]3[CH2:17][C@@H:18]([OH:30])[C@@H:19]2[NH:32][CH3:31])[CH2:11]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 86738375HCID 86738375, compound

Product 1

HCID 12961946HCID 12961946, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3β,16α-Dihydroxy-5α-androstan-17-one diacetate (18.8 g) was dissolved in a solution of methylamine in ethanol (33%; 188 ml) and the solution was stirred for 45 min. during which time a colourless solid precipitated. Sodium borohydride (10 g) was added portionwise to the stirred suspension, while keeping the temperature below 26° C. After 11/2 h. water was added and the product was filtered off and washed with water. The crude material was dissolved in methylene dichloride and the solution was washed with water, dried (MgSO4), evaporated, and the residue (16.2 g) was crystallised from ether to give 17β-methylamino-5α-androstane-3β,16α-diol 3-acetate (12.2 g) as prisms, m.p. 197°-199° C., [α]D -18° (C 1.0).

Workup

  1. customprecipitated
  2. additionSodium borohydride (10 g) was added portionwise to the stirred suspension
  3. customthe temperature below 26° C
  4. additionAfter 11/2 h. water was added
  5. filtrationthe product was filtered off
  6. washwashed with water
  7. dissolutionThe crude material was dissolved in methylene dichloride
  8. washthe solution was washed with water
  9. dry with materialdried (MgSO4)
  10. customevaporated
  11. customthe residue (16.2 g) was crystallised from ether

Sources & evidence

ORD record
ord-cc653d5e33544e66b1095cbe8445cfff
Source dataset
uspto-grants-1982_05
Patent number
US04330539

Reaction notes

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