Pyridine → 6alpha,7alpha-Diepoxy-21,21-dimethoxy-20-methylpregn-4-ene-3beta-yl acetate

HRID 1708785Notes

Reaction equation

HRID 1708785 reaction equation
[O:1]1[C:24]2=[C:25]3[C@:20]([CH3:27])([CH2:21][CH2:22][C@@H:23]2[OH:26])[C@@H:19]2[C@H:4]([C@H:5]4[C@:16]([CH3:28])([CH2:17][CH2:18]2)[C@@H:8]([CH:9]([CH3:15])[CH:10]([O:13][CH3:14])[O:11][CH3:12])[CH2:7][CH2:6]4)[C@@H:3]2[O:29][C@:2]123.N1C=CC=CC=1.[C:36](OC(=O)C)(=[O:38])[CH3:37]>C(Cl)Cl>[C:36]([O:26][C@H:23]1[CH2:22][CH2:21][C@@:20]2([CH3:27])[C:25]3[C@:2]4([O:1][C:24]1=3)[O:29][C@H:3]4[C@@H:4]1[C@@H:19]2[CH2:18][CH2:17][C@@:16]2([CH3:28])[C@H:5]1[CH2:6][CH2:7][C@@H:8]2[CH:9]([CH3:15])[CH:10]([O:13][CH3:14])[O:11][CH3:12])(=[O:38])[CH3:37]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 867458226alpha,7alpha-Diepoxy-21,21-dimethoxy-20-methylpregn-4-en-3beta-ol

Product 1

HCID 867482226alpha,7alpha-Diepoxy-21,21-dimethoxy-20-methylpregn-4-ene-3beta-yl acetateYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 0.202 g (0.50 mmole) of 1α,2α;6α,7α-diepoxy-21,21-dimethoxy-20-methylpregn-4-en-3β-ol, 0.5 ml (6.18 mmoles) of dry pyridine and 10 ml of methylene chloride was gradually added 0.1 ml (1.06 mmoles) of acetic anhydride dropwise at a temperature of 0° C. and the resulting solution was stirred at room temperature for 14 hours. The reaction mixture was then worked up in the same manner as Example 10 to recover 0.185 g of 1α,2α;6α,7α-diepoxy-21,21-dimethoxy-20-methylpregn-4-ene-3β-yl acetate (yield: 83%).

Workup

  1. customdropwise at a temperature of 0° C.
  2. customto recover 0.185 g of 1α,2α

Sources & evidence

ORD record
ord-3e25efb7173c401fb0342cf35db3ff1e
Source dataset
uspto-grants-1994_10
Patent number
US05359055

Reaction notes

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