Cyclohexanone → HCID 70501953, compound

HRID 223300Notes

Reaction equation

HRID 223300 reaction equation
[C:1]1(=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C([BH3-])#N.[Na+].[NH2:12][C@@H:13]1[CH2:30][C@@:28]2([CH3:29])[C@@H:24]([CH2:25][CH2:26][C@@H:27]2[C:31]([O:33][CH3:34])=[O:32])[C@H:23]2[C@H:14]1[C@:15]1([CH3:36])[C@H:20]([CH2:21][CH2:22]2)[CH2:19][C@H:18]([OH:35])[CH2:17][CH2:16]1>C(O)C.C([O-])(O)=O.[Na+]>[CH:1]1([NH:12][C@@H:13]2[CH2:30][C@@:28]3([CH3:29])[C@@H:24]([CH2:25][CH2:26][C@@H:27]3[C:31]([O:33][CH3:34])=[O:32])[C@H:23]3[C@H:14]2[C@:15]2([CH3:36])[C@H:20]([CH2:21][CH2:22]3)[CH2:19][C@H:18]([OH:35])[CH2:17][CH2:16]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 7967CyclohexanoneHCID 5003444Sodium cyanoborohydrideHCID 12804603HCID 12804603, compound

Product 1

HCID 70501953HCID 70501953, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 516892Sodium BicarbonateSolvent

Procedure

Cyclohexanone (2.9 ml) and sodium cyanoborohydride (2.512 g) were added to a stirred solution of methyl 11α-amino-3α-hydroxy-5β-androstane-17β-carboxylate (2.505 g) in ethanol (30 ml). After 5 h the mixture was diluted with 5% NaHCO3 solution and extracted with ether (×2). The extract was washed with water (×2), dried Na2SO4) and evaporated to leave a froth (2.544 g). A sample (0.39 g) was purified by preparative t.l.c. using CHCl3 :MeOH (19:1) to give the title compound [α]D -9°, νmax 1725 cm-1.

Workup

  1. extractionextracted with ether (×2)
  2. washThe extract was washed with water (×2), dried Na2SO4) and
  3. customevaporated
  4. customto leave a froth (2.544 g)
  5. customA sample (0.39 g) was purified by preparative t.l.c

Sources & evidence

ORD record
ord-b7fbe80042f9480abe23a129b6c0ada1
Source dataset
uspto-grants-1982_10
Patent number
US04352798

Reaction notes

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