17beta-Formyl-6-t-butylcarboxy-6-azaandrost-4-en-3-one → 17beta-(1-Hydroxy-3-methylbutyl)-6-t-butylcarboxy-6-azaandrost-4-en-3-one

HRID 1077593Notes

Reaction equation

HRID 1077593 reaction equation
[CH:1]([C@H:3]1[CH2:11][CH2:10][C@H:9]2[C@H:12]3[C@H:22]([CH2:23][CH2:24][C@:4]12[CH2:5][C:6]([OH:8])=[O:7])[C@:20]1([CH3:21])[C:15](=[CH:16][C:17](=[O:25])[CH2:18][CH2:19]1)[N:14]([C:26]([CH3:29])([CH3:28])[CH3:27])[CH2:13]3)=[O:2].[CH2:30]([Mg]Br)[CH:31]([CH3:33])[CH3:32]>C1COCC1>[OH:2][CH:1]([C@H:3]1[CH2:11][CH2:10][C@H:9]2[C@H:12]3[C@H:22]([CH2:23][CH2:24][C@:4]12[CH2:5][C:6]([OH:8])=[O:7])[C@:20]1([CH3:21])[C:15](=[CH:16][C:17](=[O:25])[CH2:18][CH2:19]1)[N:14]([C:26]([CH3:29])([CH3:28])[CH3:27])[CH2:13]3)[CH2:30][CH:31]([CH3:33])[CH3:32]

Participants

4

Reactant 2

HCID 8674970717beta-Formyl-6-t-butylcarboxy-6-azaandrost-4-en-3-oneHCID 178418816HCID 178418816, compound

Product 1

HCID 8674970817beta-(1-Hydroxy-3-methylbutyl)-6-t-butylcarboxy-6-azaandrost-4-en-3-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 17β-formyl-6-t-butylcarboxy-6-azaandrost-4-en-3-one (550 mg, 1.37 mmol), prepared in part B above, in THF (10 mL) is treated with isobutylmagnesium bromide (2.0M in diethyl ether, 2.0 mL, 4.0 mmol) at 0° C. After 20 minutes the reaction is quenched with saturated aqueous NaHSO4, extracted with ethyl acetate (2×40 mL), dried over MgSO4, concentrated and chromatographed on silica gel (50% ethyl acetate/hexanes) to give crude 17β-(1-hydroxy-3-methylbutyl)-6-t-butylcarboxy-6-azaandrost-4-en-3-one of sufficient purity to carry on to the following steps; yield: 168 mg (26%); FAB mass spec. MH+ 460.

Workup

  1. customAfter 20 minutes the reaction is quenched with saturated aqueous NaHSO4
  2. extractionextracted with ethyl acetate (2×40 mL)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customchromatographed on silica gel (50% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-befdfc19b3ac4184b2aef00b52736117
Source dataset
uspto-grants-1996_08
Patent number
US05543406

Reaction notes

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