Pyridine → 3beta-(Cyclopentanepropionyloxy)-17beta-(cyclopropyloxy)androst-5-ene

HRID 329360Notes

Reaction equation

HRID 329360 reaction equation
[CH:1]1([O:4][C@H:5]2[CH2:10][CH2:9][C@H:8]3[C@H:11]4[C@H:21]([CH2:22][CH2:23][C@:6]23[CH3:7])[C@:19]2([CH3:20])[C:14]([CH2:15][C@@H:16]([OH:24])[CH2:17][CH2:18]2)=[CH:13][CH2:12]4)[CH2:3][CH2:2]1.C(OC(=O)C)(=O)C.N1C=CC=CC=1.[C:38]([O:41][C@H:42]1[CH2:59][CH2:58][C@@:57]2([CH3:60])[C:44](=[CH:45][CH2:46][C@@H:47]3[C@@H:56]2[CH2:55][CH2:54][C@@:52]2([CH3:53])[C@H:48]3[CH2:49][CH2:50][C@@H:51]2[O:61][CH:62]2[CH2:64][CH2:63]2)[CH2:43]1)(=[O:40])[CH3:39]>O>[CH:6]1([CH2:7][CH2:39][C:38]([O:41][C@H:42]2[CH2:59][CH2:58][C@@:57]3([CH3:60])[C:44](=[CH:45][CH2:46][C@@H:47]4[C@@H:56]3[CH2:55][CH2:54][C@@:52]3([CH3:53])[C@H:48]4[CH2:49][CH2:50][C@@H:51]3[O:61][CH:62]3[CH2:64][CH2:63]3)[CH2:43]2)=[O:40])[CH2:8][CH2:9][CH2:10][CH2:5]1.[C:57]1([CH2:58][CH2:59][C:42]([O:24][C@H:16]2[CH2:17][CH2:18][C@@:19]3([CH3:20])[C:14](=[CH:13][CH2:12][C@@H:11]4[C@@H:21]3[CH2:22][CH2:23][C@@:6]3([CH3:7])[C@H:8]4[CH2:9][CH2:10][C@@H:5]3[O:4][CH:1]3[CH2:2][CH2:3]3)[CH2:15]2)=[O:41])[CH:44]=[CH:45][CH:46]=[CH:47][CH:56]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 1488276417beta-(Cyclopropyloxy)androst-5-en-3beta-olHCID 678967543beta-Acetyloxy-17beta-(cyclopropyloxy)androst-5-ene

Product 2

HCID 678967283beta-(Cyclopentanepropionyloxy)-17beta-(cyclopropyloxy)androst-5-eneHCID 678967333beta-(Benzenepropionyloxy)-17beta-(cyclopropyloxy)androst-5-ene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

17β-(Cyclopropyloxy)androst-5-en-3β-ol is treated with acetic anhydride and pyridine. The mixture is poured into water and extracted with ethyl acetate. The ethyl acetate layer is separated and dried and the solvent is evaporated to leave as a residue, 3β-acetyloxy-17β-(cyclopropyloxy)androst-5-ene. 3β-(Cyclopentanepropionyloxy)-17β-(cyclopropyloxy)androst-5-ene and 3β-(benzenepropionyloxy)-17β-(cyclopropyloxy)androst-5-ene are obtained in a similar way using the appropriate acid chlorides.

Workup

  1. extractionextracted with ethyl acetate
  2. customThe ethyl acetate layer is separated
  3. customdried
  4. customthe solvent is evaporated
  5. customto leave as a residue

Sources & evidence

ORD record
ord-bdfbd80731cb4520bdc5223c24f1037a
Source dataset
uspto-grants-1990_01
Patent number
US04891367

Reaction notes

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