Pyridine → HCID 86746915, compound

HRID 1587021Notes

Reaction equation

HRID 1587021 reaction equation
[OH:1][C@@H:2]1[CH2:19][CH2:18][C@@:17]2([CH3:20])[C@H:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:16]2[CH2:15][C@H:14]([OH:21])[C@@:12]2([CH3:13])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[CH:22]([CH3:38])[CH2:23][CH:24]=[C:25]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:3]1.N1C=CC=CC=1.[C:45](OC(=O)C)(=[O:47])[CH3:46].C1(C)C=CC=CC=1.[CH3:59][CH2:60][O:61]CC>CN(C)C1C=CN=CC=1.O>[C:45]([O:1][C@@H:2]1[CH2:19][CH2:18][C@@:17]2([CH3:20])[C@H:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:16]2[CH2:15][C@H:14]([O:21][C:60](=[O:61])[CH3:59])[C@@:12]2([CH3:13])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[CH:22]([CH3:38])[CH2:23][CH:24]=[C:25]([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:3]1)(=[O:47])[CH3:46]

Participants

8

Reactant 5

HCID 1049PyridineHCID 1140TolueneHCID 3283Diethyl EtherHCID 7918Acetic AnhydrideHCID 86746916HCID 86746916, compound

Product 1

HCID 86746915HCID 86746915, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolvent

Procedure

A mixture of 3α, 12α-dihydroxy-17β-[(1,1-diphenyl)-1-penten-4-yl]-5β-androstane (15.6 g), pyridine (14.8 ml), acetic anhydride (57.4 ml), 4-dimethylaminopyridine (3.71 g) and toluene (60 ml) is stirred at room temperature for about 30 minutes, diluted with ether and water and the layers are separated. The organic solution is washed water, dried over magnesium sulfate, filtered and concentrated in vacuo. The crude product is crystallized from 25% ether in hexane to give the desired product as an off-white solid.

Workup

  1. customthe layers are separated
  2. washThe organic solution is washed water
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product is crystallized from 25% ether in hexane

Sources & evidence

ORD record
ord-da220a22042b4adc8dc6a73203085945
Source dataset
uspto-grants-1993_06
Patent number
US05216015

Reaction notes

Loading…