Réaction #95330

ord-7a6466892cb34466b545ce9180b8985b

Équation de réaction

CCC[C@]1(O)CC[C@H]2[C@@H]3CC[C@H]4CC(=O)C[C@H](C)[C@]4(C)[C@H]3CC[C@@]21C
17β-hydroxy-1α-methyl-17α-n-propyl-5α-androstan-3-one
CC(=O)OC(C)=O
acetic anhydride
→
CCC[C@]1(OC(C)=O)CC[C@H]2[C@@H]3CC[C@H]4CC(=O)C[C@H](C)[C@]4(C)[C@H]3CC[C@@]21C
17β-acetoxy-1α-methyl-17α-n-propyl-5α-androstan-3-one

Réactifs

CCC[C@]1(O)CC[C@H]2[C@@H]3CC[C@H]4CC(=O)C[C@H](C)[C@]4(C)[C@H]3CC[C@@]21C
17β-hydroxy-1α-methyl-17α-n-propyl-5α-androstan-3-one
CC(=O)OC(C)=O
acetic anhydride

Réactifs

CN(C)c1ccncc1
4-dimethylaminopyridine

Solvants

c1ccncc1
pyridine

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    AutreAfter the mixture has been precipitated into ice water
  2. 2
    Autrerecrystallized from hexane

Mode opératoire

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.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US04344941uspto-grants-1982_08