Sodium borohydride → HCID 15085907, compound

HRID 1089422Notes

Reaction equation

HRID 1089422 reaction equation
[CH:1]1([N:4]=[C:5]2[CH2:10][CH2:9][C@H:8]3[C@H:11]4[C@H:21]([CH2:22][CH2:23][C@:6]23[CH3:7])[C@:19]2([CH3:20])[C:14]([C:15]([F:32])([F:31])[C@@H:16]([O:24][CH:25]3[CH2:30][CH2:29][CH2:28][CH2:27][O:26]3)[CH2:17][CH2:18]2)=[CH:13][CH2:12]4)[CH2:3][CH2:2]1.[BH4-].[Na+]>C(O)C>[CH:1]1([NH:4][C@H:5]2[CH2:10][CH2:9][C@H:8]3[C@H:11]4[C@H:21]([CH2:22][CH2:23][C@:6]23[CH3:7])[C@:19]2([CH3:20])[C:14]([C:15]([F:32])([F:31])[C@@H:16]([O:24][CH:25]3[CH2:30][CH2:29][CH2:28][CH2:27][O:26]3)[CH2:17][CH2:18]2)=[CH:13][CH2:12]4)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 15085906HCID 15085906, compound

Product 1

HCID 15085907HCID 15085907, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 9.1 g of 17-(cyclopropylimino)-4,4-difluoro-3β-(2-tetrahydropyranyloxy)androst-5-ene in 200 ml of dry ethanol is added 2 g of sodium borohydride. The reaction mixture is stirred at room temperature for 3 hours and then 100 ml of solvent is removed from the mixture under reduced pressure. The reaction mixture is then quenched with dilute acetic acid, diluted with 600 ml of water, and the pH is adjusted to 14 by the addition of sodium hydroxide. The aqueous mixture is extracted 3 times with 600 ml potions of ethyl acetate and the combined organic extracts are dried over magnesium sulfate. Removal of the solvent under reduced pressure gives the desired 17β-(cyclopropylamino)-4,4-difluoro-3β-(2-tetrahydropyranyloxy)androst-5-ene as a white solid. This material is treated with a catalytic amount of hydrochloric acid in dioxane to remove the tetrahydropyranyl protecting group. This compound has the following structural formula: ##STR4##

Workup

  1. custom100 ml of solvent is removed from the mixture under reduced pressure
  2. customThe reaction mixture is then quenched with dilute acetic acid
  3. additiondiluted with 600 ml of water
  4. additionthe pH is adjusted to 14 by the addition of sodium hydroxide
  5. extractionThe aqueous mixture is extracted 3 times with 600 ml potions of ethyl acetate
  6. dry with materialthe combined organic extracts are dried over magnesium sulfate
  7. customRemoval of the solvent under reduced pressure

Sources & evidence

ORD record
ord-e2af2e076179459ca62307f6ccc235f4
Source dataset
uspto-grants-1990_10
Patent number
US04966898

Reaction notes

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