Sodium borohydride → HCID 70146745, compound

HRID 840179Notes

Reaction equation

HRID 840179 reaction equation
[CH:1]1([O: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]([NH:15][C:16](=[O:24])[CH2:17][CH2:18]2)=[CH:13][C:12]4=[O:25])[CH2:3][CH2:2]1.[BH4-].[Na+]>C1COCC1.C(O)C.CCOC(C)=O>[CH:1]1([O: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]([NH:15][C:16](=[O:24])[CH2:17][CH2:18]2)=[CH:13][C@@H:12]4[OH:25])[CH2:3][CH2:2]1

Participants

6

Reactant 2

HCID 4311764Sodium borohydrideHCID 70144601HCID 70144601, compound

Product 1

HCID 70146745HCID 70146745, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolvent2×HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

17β-Cyclopropyloxy-4-aza-androst-5-en-3,7-dione (1.000 g, 2.9115 mmol) prepared in Example 18B or otherwise obtained, dissolved in a mixture of THF (25 mL) and ethanol (25 mL) is added to a solution of sodium borohydride (NaBH4; 1.000 g, 26.43 mmol) in ethanol (50 mL). The reaction mixture is stirred 5 hours at ambient temperature. At the end of this time, the reaction solution is diluted with EtOAc (100 mL) and washed with brine (NaCl; 3×100 mL). The organic solution is dried over MgSO4, filtered, concentrated and purified by flash chromatography (1:1 EtOAc/CH2Cl2) to give the title compound.

Workup

  1. washwashed with brine (NaCl; 3×100 mL)
  2. dry with materialThe organic solution is dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified by flash chromatography (1:1 EtOAc/CH2Cl2)

Sources & evidence

ORD record
ord-6af7be19edf043368de5d4cbcdbe8ec3
Source dataset
uspto-grants-2002_04
Patent number
US06365597B1

Reaction notes

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