Diisobutylaluminumhydride → 17beta-Hydroxymethyl-3beta-hydroxy-6-t-butylcarboxy-6-azaandrost-4-ene

HRID 1077591Notes

Reaction equation

HRID 1077591 reaction equation
[C:1]([C@H:5]1[CH2:13][CH2:12][C@H:11]2[C@H:14]3[C@H:24]([CH2:25][CH2:26][C@:6]12[CH2:7][C:8]([OH:10])=[O:9])[C@:22]1([CH3:23])[C:17](=[CH:18][C:19](=[O:27])[CH2:20][CH2:21]1)[N:16]([C:28]([CH3:31])([CH3:30])[CH3:29])[CH2:15]3)(OC)=[O:2].[H-].C([Al+]CC(C)C)C(C)C>C(Cl)Cl>[OH:2][CH2:1][C@H:5]1[CH2:13][CH2:12][C@H:11]2[C@H:14]3[C@H:24]([CH2:25][CH2:26][C@:6]12[CH2:7][C:8]([OH:10])=[O:9])[C@:22]1([CH3:23])[C:17](=[CH:18][C@@H:19]([OH:27])[CH2:20][CH2:21]1)[N:16]([C:28]([CH3:31])([CH3:30])[CH3:29])[CH2:15]3

Participants

4

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 8674903517beta-Carbomethoxy-6-t-butylcarboxy-6-azaandrost-4-en-3-one

Product 1

HCID 8674970617beta-Hydroxymethyl-3beta-hydroxy-6-t-butylcarboxy-6-azaandrost-4-ene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 17β-carbomethoxy-6-t-butylcarboxy-6-azaandrost-4-en-3-one (2.30 g, 5.33 mmol), Example 3, 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 17β-hydroxymethyl-3β-hydroxy-6-t-butylcarboxy-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-49054d83773444c0aac174ca65c38a53
Source dataset
uspto-grants-1996_08
Patent number
US05543406

Reaction notes

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