Dichloromethane → HCID 22804191, compound

HRID 866766Notes

Reaction equation

HRID 866766 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].C(Cl)Cl.[OH-].[Na+].[BH4-].[Na+]>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 4

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 22804192HCID 22804192, compound

Product 1

HCID 22804191HCID 22804191, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

25 g. (0.056 mole) of 2β-chloro-3α-hydroxy-17-oxo-16β-piperidino-5α-androstane-hydrochloride 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 and at a temperature of 15°-20° C. 12.5 g. (0.33 mole) of sodium borohydride are 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 2 fractions are combined, dried in vacuo at 50° C, followed by recrystallization from acetone.

Workup

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

Sources & evidence

ORD record
ord-b19a0edada6540ecb3f205447e9ed5aa
Source dataset
uspto-grants-1978_07
Patent number
US04101545

Reaction notes

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