HCID 67615161, compound → HCID 53807267, compound

HRID 726136Notes

Reaction equation

HRID 726136 reaction equation
[OH:1][CH2:2][C@H:3]1[CH2:8][CH2:7][C@H:6]2[C@H:9]3[C@H:19]([CH2:20][CH2:21][C@:4]12[CH3:5])[C@:17]1([CH3:18])[C:12](=[CH:13][C@@H:14]([OH:22])[CH2:15][CH2:16]1)[N:11]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:10]3>C(Cl)(Cl)Cl.[O-2].[Mn+4].[O-2]>[OH:1][CH2:2][C@H:3]1[CH2:8][CH2:7][C@H:6]2[C@H:9]3[C@H:19]([CH2:20][CH2:21][C@:4]12[CH3:5])[C@:17]1([CH3:18])[C:12](=[CH:13][C:14](=[O:22])[CH2:15][CH2:16]1)[N:11]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:10]3

Participants

4

Reactant 1

HCID 67615161HCID 67615161, compound

Product 1

HCID 53807267HCID 53807267, compound

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6212ChloroformSolvent

Procedure

A solution of 17β-Hydroxymethyl-3b-hydroxy-6-t-butoxycarbonyl-6-azaandrost-4-ene (prepared as described in Example 5 above), in chloroform (250 mL) is treated with activated manganese(IV) oxide. After stirring 3.5 h, the manganese salts are removed by filtration through Celite. The solution is concentrated and chromatographed on silica gel (50% ethyl acetate/hexanes) to give 17β-hydroxymethyl-6-t-butoxycarbonyl-6-azaandrost-4-en-3-one of sufficient purity to carry on to subsequent steps; yield 9.75 g (98%).

Workup

  1. customthe manganese salts are removed by filtration through Celite
  2. concentrationThe solution is concentrated
  3. customchromatographed on silica gel (50% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-2de128dc3c2644f2acf15e726b3d5ee9
Source dataset
uspto-grants-1998_01
Patent number
US05708001

Reaction notes

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