(E)-21-hydroxymethyl-21-methyl-5beta-pregn-20-ene-3beta,14beta-diol → (E)-3beta,14beta-dihydroxy-21-methyl-5beta-pregn-20-ene-21-carboxaldehyde

HRID 725262Notes

Reaction equation

HRID 725262 reaction equation
[OH:1][CH2:2]/[C:3](/[CH3:26])=[CH:4]/[C@@H:5]1[C@:22]2([CH3:23])[C@@:8]([OH:25])([C@H:9]3[C@H:19]([CH2:20][CH2:21]2)[C@:17]2([CH3:18])[C@@H:12]([CH2:13][C@@H:14]([OH:24])[CH2:15][CH2:16]2)[CH2:11][CH2:10]3)[CH2:7][CH2:6]1>C(Cl)(Cl)Cl.O=[Mn]=O>[OH:24][C@H:14]1[CH2:15][CH2:16][C@@:17]2([CH3:18])[C@H:12]([CH2:11][CH2:10][C@@H:9]3[C@@H:19]2[CH2:20][CH2:21][C@@:22]2([CH3:23])[C@:8]3([OH:25])[CH2:7][CH2:6][C@@H:5]2/[CH:4]=[C:3](\[CH3:26])/[CH:2]=[O:1])[CH2:13]1

Participants

4

Reactant 1

HCID 10690052(E)-21-hydroxymethyl-21-methyl-5beta-pregn-20-ene-3beta,14beta-diol

Product 1

HCID 10666253(E)-3beta,14beta-dihydroxy-21-methyl-5beta-pregn-20-ene-21-carboxaldehydeYield 89.8%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6212ChloroformSolvent

Procedure

To a solution of 8.40 g of (E)-21-hydroxymethyl-21-methyl-5β-pregn-20-ene-3β,14β-diol in 200 ml of chloroform, 84.0 g of MnO2 were added at room temperature. The mixture was stirred overnight and then filtered through Celite. The organic solution was evaporated to dryness to give 7.50 g of the title compound (II-a) as an off-white solid.

Workup

  1. filtrationfiltered through Celite
  2. customThe organic solution was evaporated to dryness

Sources & evidence

ORD record
ord-2fe86dca213940f09a6c3bf12be6d161
Source dataset
uspto-grants-1998_01
Patent number
US05705662

Reaction notes

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