Sodium borohydride → 3alpha-Hydroxy-17beta-methoxy-5alpha-androstane

HRID 848783Notes

Reaction equation

HRID 848783 reaction equation
[BH4-].[Na+].[CH3:3][O:4][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@H:14]([CH2:15][C:16](=[O:24])[CH2:17][CH2:18]1)[CH2:13][CH2:12]3>C(O)(C)C>[OH:24][C@@H:16]1[CH2:17][CH2:18][C@@:19]2([CH3:20])[C@@H:14]([CH2:13][CH2:12][C@@H:11]3[C@@H:21]2[CH2:22][CH2:23][C@@:6]2([CH3:7])[C@H:8]3[CH2:9][CH2:10][C@@H:5]2[O:4][CH3:3])[CH2:15]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 1104493517beta-Methoxy-5alpha-androstan-3-one

Product 1

HCID 128368613alpha-Hydroxy-17beta-methoxy-5alpha-androstane

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Sodium borohydride (0.37 gms.) is added to a mixture of 17β-methoxy-5α-androstan-3-one (3 gms.) and isopropylalcohol (95%, 35 ml.). The mixture is stirred at 20°-25° for one hour and then is concentrated to dryness. The residue is column chromatographed on a size C prepacked Merck silica gel column. Elution was performed with ethyl acetate:cyclohexane, 10:90. 6 Ml. fractions are collected. The appropriate fractions (TLC) are combined and concentrated to dryness. The residue is recrystallized from isopropyl ether to give 3α-hydroxy-17β-methoxy-5α-androstane, m.p. 164°-167°; IR (mull) 3290, 3220, 1120, 1110, 1005 cm-1 ; NMR (CDCl3) 0.72, 0.76, 0.9-2.0, 3.21, 3.3, and 4.01 δ and 3β-hydroxy-17β-methoxy-5α-androstane, m.p. 150°-152°; NMR (CDCl3) 0.75-2.0, 3.25, 3.37 and 3.6 δ.

Workup

  1. concentrationis concentrated to dryness
  2. customchromatographed on a size C
  3. washElution
  4. customfractions are collected
  5. concentrationconcentrated to dryness
  6. customThe residue is recrystallized from isopropyl ether

Sources & evidence

ORD record
ord-bfcf29539a0d42edac5b7214a999a796
Source dataset
uspto-grants-1981_10
Patent number
US04297350

Reaction notes

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