4-Pyrrolidinopyridine → HCID 18652194, compound

HRID 1587028Notes

Reaction equation

HRID 1587028 reaction equation
[Si:1]([O:18][C@@H:19]1[CH2:36][CH2:35][C@@:34]2([CH3:37])[C@H:21]([CH2:22][CH2:23][C@@H:24]3[C@@H:33]2[CH2:32][C@H:31]([OH:38])[C@@:29]2([CH3:30])[C@H:25]3[CH2:26][CH2:27][C@@H:28]2[CH:39]([CH3:55])[CH2:40][CH:41]=[C:42]([C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)[C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[CH2:20]1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1(C2C=CN=CC=2)CCCC1.[CH3:67][C:68]([CH3:74])([CH2:72][CH3:73])[C:69](Cl)=[O:70]>N1C=CC=CC=1.CCOCC.CCCCCC>[Si:1]([O:18][C@@H:19]1[CH2:36][CH2:35][C@@:34]2([CH3:37])[C@H:21]([CH2:22][CH2:23][C@@H:24]3[C@@H:33]2[CH2:32][C@H:31]([O:38][C:69](=[O:70])[C:68]([CH3:74])([CH3:67])[CH2:72][CH3:73])[C@@:29]2([CH3:30])[C@H:25]3[CH2:26][CH2:27][C@@H:28]2[CH:39]([CH3:55])[CH2:40][CH:41]=[C:42]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)[CH2:20]1)([C:14]([CH3:16])([CH3:15])[CH3:17])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 755674-PyrrolidinopyridineHCID 799582,2-Dimethylbutyryl chloride2×HCID 18652195HCID 18652195, compound

Product 1

HCID 18652194HCID 18652194, compound

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 3283Diethyl EtherSolventHCID 8058HexaneSolvent

Conditions

Temperature
110 °C

Procedure

3α-tert-butyldiphenylsilyloxy-17β-[(1,1-diphenyl)-1-penten-4-yl]-12α-hydroxy-5β-androstane (10.6 g), 4-pyrrolidinopyridine (0.207 g) and 2,2-dimethylbutyryl chloride (2.25 g) are dissolved in pyridine (55 ml) and the solution warmed to 110° C., stirred for about 1 hour, additional 2,2-dimethylbutyryl chloride (2.25 g) is added and stirring continued for about 14 hours at 110° C. The mixture is cooled, diluted with 20% ether in hexane and washed with water, then 1M hydrochloric acid. The organic solution is dried over magnesium sulfate, filtered and concentrated in vacuo. The crude product is purified by flash chromatography in 10% ether in hexane to give the desired product.

Workup

  1. stirringstirring
  2. waitcontinued for about 14 hours at 110° C
  3. temperatureThe mixture is cooled
  4. washwashed with water
  5. dry with materialThe organic solution is dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product is purified by flash chromatography in 10% ether in hexane

Sources & evidence

ORD record
ord-34635c38fa9f42c89017e4f98586fa02
Source dataset
uspto-grants-1993_06
Patent number
US05216015

Reaction notes

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