Sodium borohydride → HCID 9862308, compound

HRID 1461550Notes

Reaction equation

HRID 1461550 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]([CH2:15][C@@H:16]([OH:24])[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]([CH2:15][C@@H:16]([OH:24])[CH2:17][CH2:18]2)=[CH:13][CH2:12]4)[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 15009206HCID 15009206, compound

Product 1

HCID 9862308HCID 9862308, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 9.1 g of 17-(cyclopropylimino)androst5-en-3β-ol in 200 ml of dry ethanol was added 2 g of sodium borohydride. The reaction mixture was stirred at room temperature for 3 hours and then 100 ml of solvent was removed from the mixture under reduced pressure The reaction mixture was then quenched with dilute acetic acid, diluted with 600 ml of water, and the pH was adjusted to 14 by the addition of sodium hydroxide. The aqueous mixture was extracted 3 times with 600 ml potions of ethyl acetate and the combined organic extracts were dried over magnesium sulfate. Removal of the solvent under reduced pressure gave the desired 17β-(cyclopropylamino)androst-5-en-3β-ol as a white solid; MS (m/z): 370 (M+41)+, 358 (M+29)+, 330(M+H)+, 312 (MH-H2O)+.

Workup

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

Sources & evidence

ORD record
ord-19bb08e809474a44bf5e80b12a0e6dca
Source dataset
uspto-grants-1991_12
Patent number
US05075464

Reaction notes

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