Pyridine → HCID 15085902, compound

HRID 1089426Notes

Reaction equation

HRID 1089426 reaction equation
[F:1][C:2]1([F:26])[C@@H:19]([OH:20])[CH2:18][CH2:17][C@@:16]2([CH3:21])[C:3]1=[CH:4][CH2:5][C@@H:6]1[C@@H:15]2[CH2:14][CH2:13][C@@:11]2([CH3:12])[C@H:7]1[CH2:8][CH2:9][C@@H:10]2[O:22][CH:23]1[CH2:25][CH2:24]1.C(OC(=O)C)(=O)C.N1C=CC=CC=1.[C:40]([O:43][C@H:44]1[CH2:61][CH2:60][C@@:59]2([CH3:62])[C:46](=[CH:47][CH2:48][C@@H:49]3[C@@H:58]2[CH2:57][CH2:56][C@@:54]2([CH3:55])[C@H:50]3[CH2:51][CH2:52][C@@H:53]2[O:63][CH:64]2[CH2:66][CH2:65]2)[C:45]1([F:68])[F:67])(=[O:42])[CH3:41]>O>[CH:7]1([CH2:6][CH2:41][C:40]([O:43][C@H:44]2[CH2:61][CH2:60][C@@:59]3([CH3:62])[C:46](=[CH:47][CH2:48][C@@H:49]4[C@@H:58]3[CH2:57][CH2:56][C@@:54]3([CH3:55])[C@H:50]4[CH2:51][CH2:52][C@@H:53]3[O:63][CH:64]3[CH2:65][CH2:66]3)[C:45]2([F:67])[F:68])=[O:42])[CH2:11][CH2:10][CH2:9][CH2:8]1.[C:59]1([CH2:60][CH2:61][C:44]([O:20][C@H:19]2[CH2:18][CH2:17][C@@:16]3([CH3:21])[C:3](=[CH:4][CH2:5][C@@H:6]4[C@@H:15]3[CH2:14][CH2:13][C@@:11]3([CH3:12])[C@H:7]4[CH2:8][CH2:9][C@@H:10]3[O:22][CH:23]3[CH2:24][CH2:25]3)[C:2]2([F:26])[F:1])=[O:43])[CH:46]=[CH:47][CH:48]=[CH:49][CH:58]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 15085897HCID 15085897, compoundHCID 15085901HCID 15085901, compound

Product 2

HCID 15085902HCID 15085902, compoundHCID 15085903HCID 15085903, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4,4-Difluoro-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-4,4-difluoro-17β-(cyclopropyloxy)androst-5-ene. 3β-(Cyclopentanepropionyloxy)-4,4-difluoro-17β-(cyclopropyloxy)androst-5-ene and 3β-(benzenepropionyloxy)-4,4-difluoro-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-a81193e0660c44fc8e0a23bacc2bfbc7
Source dataset
uspto-grants-1990_10
Patent number
US04966897

Reaction notes

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