Water → HCID 70501595, compound

HRID 543643Notes

Reaction equation

HRID 543643 reaction equation
[BH4-].[Na+].[C:3]([O:6][C@H:7]1[CH2:24][C@@:23]2([CH3:25])[C@@H:10]([CH2:11][CH2:12][C@@H:13]3[C@@H:22]2[CH2:21][CH2:20][C@@:18]2([CH3:19])[C@H:14]3[CH2:15][C@H:16]([N:27]3[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]3)[C:17]2=[O:26])[CH2:9][CH2:8]1)(=[O:5])[CH3:4].O>CO>[C:3]([O:6][C@H:7]1[CH2:24][C@@:23]2([CH3:25])[C@@H:10]([CH2:11][CH2:12][C@@H:13]3[C@@H:22]2[CH2:21][CH2:20][C@@:18]2([CH3:19])[C@H:14]3[CH2:15][C@H:16]([N:27]3[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]3)[C@@H:17]2[OH:26])[CH2:9][CH2:8]1)(=[O:5])[CH3:4]

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 70501191HCID 70501191, compound

Product 1

HCID 70501595HCID 70501595, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (9.40 g) was added portionwise to a stirred solution of 2β-acetyloxy-16β-(1-piperidinyl)-5α-androstan-17-one (46.99 g) in methanol (235 ml). After 1 h, water (300 ml) was added to precipitate the product as a gum, which was extracted into diethyl ether (300 ml). The extract was washed neutral with water (3×300 ml), dried (MgSO4) and evaporated to dryness. Crystallisation of the residue from methanol afforded 16β-(1-piperidinyl)-5α-androstane-2β,17β-diol 2-acetate (25.49 g), m.p. 162°-166° C., [α]D +29.1° (c 0.45 in CHCl3).

Workup

  1. customto precipitate the product as a gum, which
  2. extractionwas extracted into diethyl ether (300 ml)
  3. washThe extract was washed neutral with water (3×300 ml)
  4. dry with materialdried (MgSO4)
  5. customevaporated to dryness
  6. customCrystallisation of the residue from methanol

Sources & evidence

ORD record
ord-c1162d09f98740188451c4b6923d719b
Source dataset
uspto-grants-1984_05
Patent number
US04447425

Reaction notes

Loading…