Methanol → HCID 57901185, compound

HRID 2221427Notes

Reaction equation

HRID 2221427 reaction equation
[Cl:1][C:2]1[CH:27]=[CH:26][C:5]([O:6][CH2:7][C@H:8]([O:21]S(C)(=O)=O)[CH2:9][N:10]2[C:14](=[O:15])[C:13]3=[CH:16][CH:17]=[CH:18][CH:19]=[C:12]3[C:11]2=[O:20])=[C:4](OC(=O)C)[CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].CO>C(OCC)(=O)C>[Cl:1][C:2]1[CH:27]=[CH:26][C:5]2[O:6][CH2:7][C@H:8]([CH2:9][N:10]3[C:14](=[O:15])[C:13]4=[CH:16][CH:17]=[CH:18][CH:19]=[C:12]4[C:11]3=[O:20])[O:21][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 10340Sodium CarbonateHCID 86602741HCID 86602741, compound

Product 1

HCID 57901185HCID 57901185, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

To a reaction vessel were added crude (R)-1-(4-chloro-2-acetoxyphenoxy)-2-methanesulfonyloxy-3-phthalimidopropane 242 mg (0.50 mmol), sodium carbonate 58.3 mg (0.60 mmol) and methanol 2 mL, and the mixture was stirred at 50° C. for 9 hours. To the reaction mixture was added ethyl acetate and the mixture was washed with water. The solvent was evaporated and recrystallized to give (S)-7-chloro-2-(phthalimidomethyl)-1,4-benzodioxane 114 mg (yield 70%, chemical purity 98%, optical purity 98% ee) as a white solid.

Workup

  1. washthe mixture was washed with water
  2. customThe solvent was evaporated
  3. customrecrystallized

Sources & evidence

ORD record
ord-8baeef7c80e24495b453986460ab1b35
Source dataset
uspto-grants-2008_05
Patent number
US07368608B2

Reaction notes

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