Hydrochloric Acid → HCID 70477354, compound

HRID 462438Notes

Reaction equation

HRID 462438 reaction equation
[CH3:1][CH:2]([CH3:6])[CH2:3][CH:4]=O.C([BH3-])#N.[Na+].[NH2:11][C@@H:12]1[CH2:29][C@@:27]2([CH3:28])[C@@H:23]([CH2:24][CH2:25][C@@H:26]2[C:30]([O:32][CH3:33])=[O:31])[C@H:22]2[C@H:13]1[C@:14]1([CH3:35])[C@@H:19]([CH2:20][CH2:21]2)[CH2:18][C@H:17]([OH:34])[CH2:16][CH2:15]1.[BH4-].[Na+].[ClH:38]>C(O)C.C(OCC)(=O)C.CCOCC.O>[ClH:38].[OH:34][C@@H:17]1[CH2:16][CH2:15][C@@:14]2([CH3:35])[C@@H:19]([CH2:20][CH2:21][C@@H:22]3[C@@H:13]2[C@H:12]([NH:11][CH2:4][CH2:3][CH:2]([CH3:6])[CH3:1])[CH2:29][C@@:27]2([CH3:28])[C@H:23]3[CH2:24][CH2:25][C@@H:26]2[C:30]([O:32][CH3:33])=[O:31])[CH2:18]1

Participants

10

Reactant 5

HCID 313Hydrochloric AcidHCID 115523-MethylbutanalHCID 4311764Sodium borohydrideHCID 5003444Sodium cyanoborohydrideHCID 12804602HCID 12804602, compound

Product 1

HCID 70477354HCID 70477354, compound

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-Methylbutanal (2.62 ml) and sodium cyanoborohydride (306 mg) were added to a solution of methyl 11α-amino-3α-hydroxy-5α-androstane-17β-carboxylate (5.77 g) in ethanol (130 ml) and after 18 h sodium borohydride (0.7 g) was added. After a further 15 minutes water (350 ml) was added and the mixture was extracted with ether (×2). The extract was washed with water, dried (Na2SO4) and evaporated to leave a foam which was dissolved in ethyl acetate (200 ml). Concentrated hydrochloric acid solution (4 ml) was added to the stirred solution and the mixture was diluted with ether (200 ml). The solid formed was collected by filtration, dried and stirred with ethyl acetate (100 ml) for 0.5 h. The solid was collected and dried to give the title compound (4.82 g) m.p. dec 230°-300° C., [α]D +30°.

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with ether (×2)
  3. washThe extract was washed with water
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customto leave a foam which
  7. customThe solid formed
  8. filtrationwas collected by filtration
  9. customdried
  10. customThe solid was collected
  11. customdried

Sources & evidence

ORD record
ord-0ceb59700cf14bb58fac1a3447f9f647
Source dataset
uspto-grants-1985_05
Patent number
US04515786

Reaction notes

Loading…