17beta-Carbomethoxy-6-t-butoxycarbonyl-6-azaandrost-4-en-3-one → 17Hydroxymethyl-3-hydroxy-6-t-butoxycarbonyl-6-azaandrost-4-ene

HRID 726135Notes

Reaction equation

HRID 726135 reaction equation
[C:1]([C@H:5]1[CH2:10][CH2:9][C@H:8]2[C@H:11]3[C@H:21]([CH2:22][CH2:23][C@:6]12[CH3:7])[C@:19]1([CH3:20])[C:14](=[CH:15][C:16](=[O:24])[CH2:17][CH2:18]1)[N:13]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:12]3)(OC)=[O:2].[H-].C([Al+]CC(C)C)C(C)C>C(Cl)Cl>[OH:2][CH2:1][CH:5]1[CH2:10][CH2:9][C@H:8]2[C@H:11]3[C@H:21]([CH2:22][CH2:23][C@:6]12[CH3:7])[C@:19]1([CH3:20])[C:14](=[CH:15][CH:16]([OH:24])[CH2:17][CH2:18]1)[N:13]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:12]3

Participants

4

Reactant 2

HCID 1000287217beta-Carbomethoxy-6-t-butoxycarbonyl-6-azaandrost-4-en-3-oneHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 2288120817Hydroxymethyl-3-hydroxy-6-t-butoxycarbonyl-6-azaandrost-4-ene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 17β-carbomethoxy-6-t-butoxycarbonyl-6-azaandrost-4-en-3-one (2.30 g, 5.33 mmol), example 1, part E, in methylene chloride (70 mL) at -78° C. is treated with diisobutylaluminum hydride (1.5M in toluene, 15 mL, 22.5 mmol). After 20 minutes the reaction is quenched with methanol (4 mL), methylene chloride added (150 mL), washed with 2N NaOH and water, dried over MgSO4 and concentrated to give crude 17hydroxymethyl-3-hydroxy-6-t-butoxycarbonyl-6-azaandrost-4-ene of sufficient purity to carry on to the following steps; yield: 2.16 g (99%).

Workup

  1. customAfter 20 minutes the reaction is quenched with methanol (4 mL), methylene chloride
  2. additionadded (150 mL)
  3. washwashed with 2N NaOH and water
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-6c66fbcbf77e44e28af67cf917a3ccce
Source dataset
uspto-grants-1998_01
Patent number
US05708001

Reaction notes

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