4-Pyrrolidinopyridine → HCID 18652189, compound

HRID 1587031Notes

Reaction equation

HRID 1587031 reaction equation
[C:1]([O:4][C@@H:5]1[CH2:22][CH2:21][C@@:20]2([CH3:23])[C@H:7]([CH2:8][C@@H:9]([O:42][C:43](=[O:45])[CH3:44])[C@@H:10]3[C@@H:19]2[CH2:18][C@H:17]([OH:24])[C@@:15]2([CH3:16])[C@H:11]3[CH2:12][CH2:13][C@@H:14]2[CH:25]([CH3:41])[CH2:26][CH:27]=[C:28]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:6]1)(=[O:3])[CH3:2].N1(C2C=CN=CC=2)CCCC1.[CH3:57][C:58]([CH3:64])([CH2:62][CH3:63])[C:59](Cl)=[O:60]>N1C=CC=CC=1.CCOCC.CCCCCC>[C:1]([O:4][C@@H:5]1[CH2:22][CH2:21][C@@:20]2([CH3:23])[C@H:7]([CH2:8][C@@H:9]([O:42][C:43](=[O:45])[CH3:44])[C@@H:10]3[C@@H:19]2[CH2:18][C@H:17]([O:24][C:59](=[O:60])[C:58]([CH3:64])([CH3:57])[CH2:62][CH3:63])[C@@:15]2([CH3:16])[C@H:11]3[CH2:12][CH2:13][C@@H:14]2[CH:25]([CH3:41])[CH2:26][CH:27]=[C:28]([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH2:6]1)(=[O:3])[CH3:2]

Participants

7

Reactant 3

HCID 755674-PyrrolidinopyridineHCID 799582,2-Dimethylbutyryl chloride2×HCID 18652190HCID 18652190, compound

Product 1

HCID 18652189HCID 18652189, compound

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 3283Diethyl EtherSolventHCID 8058HexaneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 3α,7α-diacetoxy-12α-hydroxy-17β-[(1,1-diphenyl)-1-penten-4-yl]-5β-androstane (7.6 g), 4-pyrrolidinopyridine (0.184 g) and 2,2-dimethylbutyryl chloride (2.0 g) in pyridine (40 ml) is heated at 110° C. for about 1 hour, additional 2,2-dimethylbutyryl chloride (2.0 g) is added and heating is continued for about 16 hours. The mixture is cooled, diluted with 20% ether in hexane and the organic solution washed with 1.0M hydrochloric acid, saturated sodium chloride solution, dried over magnesium sulfate, filtered and concentrated in vacuo. The crude product is purified by flash chromatography in 30% ether in hexane to give the desired product.

Workup

  1. temperatureheating
  2. temperatureThe mixture is cooled
  3. washthe organic solution washed with 1.0M hydrochloric acid, saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product is purified by flash chromatography in 30% ether in hexane

Sources & evidence

ORD record
ord-8288057a53b14c10bf738318886c0d2c
Source dataset
uspto-grants-1993_06
Patent number
US05216015

Reaction notes

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