4-Pyrrolidinopyridine → HCID 18652180, compound

HRID 1587026Notes

Reaction equation

HRID 1587026 reaction equation
[Si:1]([O:8][C@@H:9]1[CH2:26][CH2:25][C@@:24]2([CH3:27])[C@H:11]([CH2:12][CH2:13][C@@H:14]3[C@@H:23]2[CH2:22][C@H:21]([OH:28])[C@@:19]2([CH3:20])[C@H:15]3[CH2:16][CH2:17][C:18]2=[O:29])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].N1(C2C=CN=CC=2)CCCC1.[CH3:41][C:42]([CH3:48])([CH2:46][CH3:47])[C:43](Cl)=[O:44]>N1C=CC=CC=1.CCOCC>[CH3:41][C:42]([CH3:48])([CH2:46][CH3:47])[C:43]([O:28][C@@H:21]1[C@@:19]2([CH3:20])[C@@H:15]([CH2:16][CH2:17][C:18]2=[O:29])[C@H:14]2[C@@H:23]([C@:24]3([CH3:27])[C@H:11]([CH2:12][CH2:13]2)[CH2:10][C@H:9]([O:8][Si:1]([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2])[CH2:26][CH2:25]3)[CH2:22]1)=[O:44]

Participants

6

Reactant 3

HCID 755674-PyrrolidinopyridineHCID 799582,2-Dimethylbutyryl chlorideHCID 67856976HCID 67856976, compound

Product 1

HCID 18652180HCID 18652180, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
85 °C

Procedure

3α-tert-butyldimethylsilyloxy-12α-hydroxy-5β-androstan-17-one (5.9 g), 4-pyrrolidinopyridine (0.30 g) and 2,2-dimethylbutyryl chloride (6 ml) are dissolved in pyridine (30 ml) and the solution warmed to 85° C., stirred at that temperature for about 3 hours, cooled, diluted with ether and washed with water, then 0.5M hydrochloric acid. The organic solution is dried over magnesium sulfate, filtered and concentrated in vacuo. The crude product is purified by flash chromatography in a gradient of 20% to 30% ether in hexane to give the desired product.

Workup

  1. temperaturecooled
  2. washwashed with water
  3. dry with materialThe organic solution is dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product is purified by flash chromatography in a gradient of 20% to 30% ether in hexane

Sources & evidence

ORD record
ord-70773146cdb641819bf0717fbb8411a0
Source dataset
uspto-grants-1993_06
Patent number
US05216015

Reaction notes

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