Sodium Hydroxide → HCID 22804191, compound

HRID 2420241Notes

Reaction equation

HRID 2420241 reaction equation
Cl.[Cl:2][C@H:3]1[CH2:20][C@@:19]2([CH3:21])[C@@H:6]([CH2:7][CH2:8][C@@H:9]3[C@@H:18]2[CH2:17][CH2:16][C@@:14]2([CH3:15])[C@H:10]3[CH2:11][C@H:12]([N:23]3[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]3)[C:13]2=[O:22])[CH2:5][C@@H:4]1[OH:29].[OH-].[Na+].[BH4-].[Na+]>C(Cl)Cl.CO>[Cl:2][C@H:3]1[CH2:20][C@@:19]2([CH3:21])[C@@H:6]([CH2:7][CH2:8][C@@H:9]3[C@@H:18]2[CH2:17][CH2:16][C@@:14]2([CH3:15])[C@H:10]3[CH2:11][C@H:12]([N:23]3[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]3)[C@@H:13]2[OH:22])[CH2:5][C@@H:4]1[OH:29]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 22804192HCID 22804192, compound

Product 1

HCID 22804191HCID 22804191, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

25 g (0.056 mole) of 2β-chloro-3α-hydroxy-17-oxo-16β-piperidino-5α-androstane-hydrochloride (Example 14) are dissolved in the mixture of 52 ml of methylene chloride and 125 ml of methanol. Under vigorous stirring 2.75 g (0.069 mole) of pulverized sodium hydroxide are added at a temperature of 15°-20° C. 12.5 g (0.33 mole) of sodium borohydride are also added to the solution. The product precipitated immediately. The crystalline solution is stirred for 5 hours, whereafter the product is filtered and washed with water. The mother liquor is evaporated at reduced pressure at a temperature of below 30° C, the residue is triturated with water, the mixture is filtered and the second crop above the filter is washed with water. The two fractions are combined, dried in vacuo at 50° C, followed by recrystallization from acetone. Yield: 20.2 g (88%) of 2β-chloro-3α,17β-dihydroxy-16β-piperidine-5α-androstane; m.p. 232°-234° C.

Workup

  1. additionare added at a temperature of 15°-20° C
  2. customThe product precipitated immediately
  3. filtrationis filtered
  4. washwashed with water
  5. customThe mother liquor is evaporated at reduced pressure at a temperature of below 30° C
  6. customthe residue is triturated with water
  7. filtrationthe mixture is filtered
  8. washthe second crop above the filter is washed with water
  9. customdried in vacuo at 50° C
  10. customfollowed by recrystallization from acetone

Sources & evidence

ORD record
ord-72065e9f7e944cf7bec5e6040448507d
Source dataset
uspto-grants-1978_08
Patent number
US04110326

Reaction notes

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