Methylamine → HCID 12962048, compound

HRID 1065697Notes

Reaction equation

HRID 1065697 reaction equation
[C:1]([O:4][C@H:5]1[CH2:22][CH2:21][C@@:20]2([CH3:23])[C:7](=[CH:8][CH2:9][C@@H:10]3[C@@H:19]2[CH2:18][CH2:17][C@@:15]2([CH3:16])[C@H:11]3[CH2:12][C@@H:13]([O:25]C(=O)C)[C:14]2=O)[CH2:6]1)(=[O:3])[CH3:2].[CH3:29][NH2:30]>>[C:1]([O:4][C@H:5]1[CH2:22][CH2:21][C@@:20]2([CH3:23])[C:7](=[CH:8][CH2:9][C@@H:10]3[C@@H:19]2[CH2:18][CH2:17][C@@:15]2([CH3:16])[C@H:11]3[CH2:12][C@@H:13]([OH:25])[C@@H:14]2[NH:30][CH3:29])[CH2:6]1)(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 6329MethylamineHCID 54289955HCID 54289955, compound

Product 1

HCID 12962048HCID 12962048, compound

Procedure

3β,16α-bis(Acetyloxy)-androst-5-en-17-one (2.04 g) was dissolved in methylamine solution (20.4 ml; 33% in methanol) and the solution was stirred at room temperature for 20 min. during which time the 17,17-methylimine crystallised out. Sodium borohydride (1.02 g) was added portionwise to the stirred suspension, keeping the temperature below 25° C. After 11/2 h., the excess methylamine was removed under reduced pressure, water (200 ml) was added, and the mixture was extracted with dichloromethane. The extracts were washed with water, dried (Na2SO4) and evaporated to give a white froth (2.07 g), crystallisation of which from dichloromethane-ether afforded pure 17β-methylamino-androst-5-ene-3β,16α-diol 3-acetate as needles, (1.74 g; 91.6%) m.p. 192°-194° C., [α]D -79.4° (c 0.75 in CHCl3).

Workup

  1. customcrystallised out
  2. additionSodium borohydride (1.02 g) was added portionwise to the stirred suspension
  3. customthe temperature below 25° C
  4. customAfter 11/2 h., the excess methylamine was removed under reduced pressure, water (200 ml)
  5. additionwas added
  6. extractionthe mixture was extracted with dichloromethane
  7. washThe extracts were washed with water
  8. dry with materialdried (Na2SO4)
  9. customevaporated
  10. customto give
  11. customa white froth (2.07 g), crystallisation of which from dichloromethane-ether afforded pure 17β-methylamino-androst-5-ene-3β,16α-diol 3-acetate as needles, (1.74 g; 91.6%) m.p. 192°-194° C., [α]D -79.4° (c 0.75 in CHCl3)

Sources & evidence

ORD record
ord-cc23f85dade143c2a70a533b97e37496
Source dataset
uspto-grants-1982_05
Patent number
US04330539

Reaction notes

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