[(2R,4R)-2-(4-methoxyphenyl)-5,5-dimethyl-1,3-dioxan-4-yl]methyl 4-nitrobenzoate → (2R)-2,4-dihydroxy-3,3-dimethylbutyl 4-nitrobenzoate

HRID 1643421Notes

Reaction equation

HRID 1643421 reaction equation
[N+:1]([C:4]1[CH:29]=[CH:28][C:7]([C:8]([O:10][CH2:11][C@H:12]2[C:17]([CH3:19])([CH3:18])[CH2:16][O:15][C@@H](C3C=CC(OC)=CC=3)[O:13]2)=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2]>C1COCC1.C(O)(=O)C>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:8]([O:10][CH2:11][C@H:12]([OH:13])[C:17]([CH3:18])([CH3:19])[CH2:16][OH:15])=[O:9])=[CH:28][CH:29]=1)([O-:3])=[O:2]

Participants

4

Reactant 1

HCID 66754235[(2R,4R)-2-(4-methoxyphenyl)-5,5-dimethyl-1,3-dioxan-4-yl]methyl 4-nitrobenzoate

Product 1

HCID 66753335(2R)-2,4-dihydroxy-3,3-dimethylbutyl 4-nitrobenzoate

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of compound obtained in Step C (4.4 g, 10.96 mmol) in THF (5 ml) and acetic acid (70%) (50 ml) was heated at 60° C. for 4 hours. The solvent was concentrated under reduced pressure and dissolved in EtOAc. The organic layer was washed with NaHCO3 and brine. The organic phase was concentrated under reduced pressure and the crude was crystallized from Et2O and n-Hexane at 0° C. to give a white solid.

Workup

  1. concentrationThe solvent was concentrated under reduced pressure
  2. dissolutiondissolved in EtOAc
  3. washThe organic layer was washed with NaHCO3 and brine
  4. concentrationThe organic phase was concentrated under reduced pressure
  5. customthe crude was crystallized from Et2O and n-Hexane at 0° C.
  6. customto give a white solid

Sources & evidence

ORD record
ord-f5d71b04f32b45f392452f615057f16e
Source dataset
uspto-grants-2012_02
Patent number
US08119806B2

Reaction notes

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