Methanol → HCID 22800113, compound

HRID 1439189Notes

Reaction equation

HRID 1439189 reaction equation
[OH:1][CH2:2][C@@:3]12[C@@H:20]3[C:11](=[C:12]4[C@@:16]([CH2:18][CH2:19]3)([CH3:17])[C@@H:15]([O:21][C:22](=[O:27])[C:23]([CH3:26])([CH3:25])[CH3:24])[CH2:14][CH2:13]4)[CH:10]=[CH:9][C:8]1=[CH:7][C:6](=[O:28])[CH2:5][CH2:4]2.CO.[BH4-].[Na+].C(=O)(O)[O-].[Na+]>C(O)(=O)C.O>[OH:28][C@H:6]1[CH2:5][CH2:4][C@@:3]2([CH2:2][OH:1])[C:8]([CH:9]=[CH:10][C:11]3[C@@H:20]2[CH2:19][CH2:18][C@@:16]2([CH3:17])[C:12]=3[CH2:13][CH2:14][C@@H:15]2[O:21][C:22](=[O:27])[C:23]([CH3:26])([CH3:25])[CH3:24])=[CH:7]1

Participants

6

Reactant 4

HCID 887MethanolHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydride2×HCID 22800109HCID 22800109, compound

Product 1

HCID 22800113HCID 22800113, compound

Reagents, catalysts & solvents 1

HCID 21899381Acetic acid--water (1/1)Solvent

Procedure

A mixture of 5 g of 19-hydroxy-17β-pivaloxyandrosta-4,6,8(14)-trien-3-one and 50 ml of methanol was cooled below 5° C. by an ice-bath, whereupon 500 mg. of sodium borohydride was added slowly and with stirring. After 85 minutes another 50 mg of sodium borohydride was added. The mixture was stirred with cooling for another 35 minutes, whereupon 10 ml of acetic acid-water 1:10 was added dropwise. After 10 minutes of further stirring without external cooling 2 g of sodium bicarbonate was added. The mixture was then concentrated at reduced pressure to a thick paste and 50 ml of water was added. The precipitate obtained was filtered and digested with benzene to yield 3β,19-dihydroxy-17β-pivaloxyandrosta-4,6,8(14)-triene, uv max 275 (sh), 285 and 300 (sh) mμ.

Workup

  1. temperaturewas cooled below 5° C. by an ice-bath, whereupon 500 mg
  2. stirringThe mixture was stirred
  3. additionwas added dropwise
  4. stirringAfter 10 minutes of further stirring
  5. additionwas added
  6. concentrationThe mixture was then concentrated at reduced pressure to a thick paste and 50 ml of water
  7. additionwas added
  8. customThe precipitate obtained
  9. filtrationwas filtered

Sources & evidence

ORD record
ord-baf24e8c668c4588990299e313916a5c
Source dataset
uspto-grants-1977_11
Patent number
US04058539

Reaction notes

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