Acetic Anhydride → 17beta-Acetoxy-1alpha-methyl-17alpha-n-propyl-5alpha-androstan-3-one

HRID 637645Notes

Reaction equation

HRID 637645 reaction equation
[OH:1][C@@:2]1([CH2:23][CH2:24][CH3:25])[CH2:7][CH2:6][C@H:5]2[C@H:8]3[C@H:18]([CH2:19][CH2:20][C@:3]12[CH3:4])[C@:16]1([CH3:17])[C@H:11]([CH2:12][C:13](=[O:22])[CH2:14][C@@H:15]1[CH3:21])[CH2:10][CH2:9]3.[C:26](OC(=O)C)(=[O:28])[CH3:27]>N1C=CC=CC=1.CN(C)C1C=CN=CC=1>[C:26]([O:1][C@@:2]1([CH2:23][CH2:24][CH3:25])[CH2:7][CH2:6][C@H:5]2[C@H:8]3[C@H:18]([CH2:19][CH2:20][C@:3]12[CH3:4])[C@:16]1([CH3:17])[C@H:11]([CH2:12][C:13](=[O:22])[CH2:14][C@@H:15]1[CH3:21])[CH2:10][CH2:9]3)(=[O:28])[CH3:27]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 71232Rosterolone

Product 1

HCID 1302088617beta-Acetoxy-1alpha-methyl-17alpha-n-propyl-5alpha-androstan-3-one

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

1.5 g of 17β-hydroxy-1α-methyl-17α-n-propyl-5α-androstan-3-one is allowed to stand at room temperature in 6 ml of pyridine with 3 ml of acetic anhydride for 16 hours, after the addition of 75 mg of 4-dimethylaminopyridine. After the mixture has been precipitated into ice water and recrystallized from hexane, 1.3 g of 17β-acetoxy-1α-methyl-17α-n-propyl-5α-androstan-3-one is obtained, m.p. 128°-129° C.

Workup

  1. customAfter the mixture has been precipitated into ice water
  2. customrecrystallized from hexane

Sources & evidence

ORD record
ord-7447c19f108d421895c8ca09ea481fa5
Source dataset
uspto-grants-1985_12
Patent number
US04558041

Reaction notes

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