HCID 19828478, compound → HCID 19828471, compound

HRID 1494526Notes

Reaction equation

HRID 1494526 reaction equation
CC1(C)[O:7][CH2:6][C:5]2[C:8]([CH:13]([O:21][C:22](=[O:24])[CH3:23])[C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=3)=[CH:9][N:10]=[C:11]([CH3:12])[C:4]=2[O:3]1>C(O)(C(F)(F)F)=O.O>[CH3:12][C:11]1[C:4]([OH:3])=[C:5]([CH2:6][OH:7])[C:8]([CH:13]([O:21][C:22](=[O:24])[CH3:23])[C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)=[CH:9][N:10]=1

Participants

3

Reactant 1

HCID 19828478HCID 19828478, compound

Product 1

HCID 19828471HCID 19828471, compound

Reagents, catalysts & solvents 1

HCID 22392675Trifluoroacetic acid waterSolvent

Procedure

0.24 g (0.66 mmoles) of (+)-2,2,8-trimethyl-5-(4-chloro-α-acetoxybenzyl)-pyrido-[4,3-e]-1,3-dioxane are poured into a 10 ml round bottomed flask and dissolved in 3.3 ml of TFA/H2O (10:1). The reaction is allowed to stir at room temperature for 1.5 hours, the solvent is then removed by rotary evaporation. 1 ml of methanolic ammonia is added to the crude product (the excess of TFA being neutralized), then evaporated to dryness under high vacuum. The crude product was shown to contain 90% of the desired diol-acetate by HPLC along with 4.4% of unreacted starting material.

Workup

  1. customthe solvent is then removed by rotary evaporation
  2. addition1 ml of methanolic ammonia is added to the crude product (the excess of TFA being
  3. customthen evaporated to dryness under high vacuum

Sources & evidence

ORD record
ord-8c32e222ef7946a19bc7c28c1fcc9760
Source dataset
uspto-grants-1991_06
Patent number
US05026855

Reaction notes

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