Water → 4,4-Dimethylandrostan-3beta,6alpha,17beta-triol

HRID 1182871Notes

Reaction equation

HRID 1182871 reaction equation
[OH:1][C@H:2]1[CH2:7][CH2:6][C@H:5]2[C@H:8]3[C@H:18]([CH2:19][CH2:20][C@:3]12[CH3:4])[C@:16]1([CH3:17])[C:11]([C:12]([CH3:23])([CH3:22])[C:13](=[O:21])[CH2:14][CH2:15]1)=[CH:10][CH2:9]3.[OH2:24]>C1COCC1>[CH3:22][C:12]1([CH3:23])[C@@H:13]([OH:21])[CH2:14][CH2:15][C@@:16]2([CH3:17])[CH:11]1[C@@H:10]([OH:24])[CH2:9][C@@H:8]1[C@@H:18]2[CH2:19][CH2:20][C@@:3]2([CH3:4])[C@H:5]1[CH2:6][CH2:7][C@@H:2]2[OH:1]

Participants

4

Reactant 2

HCID 962WaterHCID 22415617beta-Hydroxy-4,4-dimethylandrost-5-en-3-one

Product 1

HCID 687306424,4-Dimethylandrostan-3beta,6alpha,17beta-triolYield 32%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 17β-hydroxy-4,4-dimethylandrost-5-en-3-one (408 mg) in THF (12 ml) at −15° C., under N2, was added 1M BH3.THF complex in THF (6.44 ml). The mixture was then stirred at RT overnight. H2O (5 ml) was cautiously added dropwise followed by NaBO3.4H2O (330 mg). After stirring at RT overnight, the mixture was filtered. The solid was washed with THF and then discarded. The liquid phases were separated and the aqueous layer was saturated with NaCl and extracted with THF (3×200 ml). The combined organic extracts were dried over NaCl and Na2SO4, filtered and evaporated to dryness. The crude product was purified by flash chromatography (SiO2, DCM/MeOH 97/3) to give 4,4-dimethylandrostan-3β,6α,17β-triol (137 mg, 32%).

Workup

  1. stirringAfter stirring at RT overnight
  2. filtrationthe mixture was filtered
  3. washThe solid was washed with THF
  4. customThe liquid phases were separated
  5. extractionextracted with THF (3×200 ml)
  6. dry with materialThe combined organic extracts were dried over NaCl and Na2SO4
  7. filtrationfiltered
  8. customevaporated to dryness
  9. customThe crude product was purified by flash chromatography (SiO2, DCM/MeOH 97/3)

Sources & evidence

ORD record
ord-b236d12953e4443388be547402245801
Source dataset
uspto-grants-2014_03
Patent number
US08664210B2

Reaction notes

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