Chloromethyl Methyl Ether → Methyl 2-(1-tert-Butoxycarbonylpiperidin-4-yloxy)-4-(methoxymethoxy)benzoate

HRID 644293Notes

Reaction equation

HRID 644293 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:24]=[C:23]([OH:25])[CH:22]=[CH:21][C:16]=2[C:17]([O:19][CH3:20])=[O:18])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH3:32][O:33][CH2:34]Cl>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:24]=[C:23]([O:25][CH2:32][O:33][CH3:34])[CH:22]=[CH:21][C:16]=2[C:17]([O:19][CH3:20])=[O:18])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl Ether2×HCID 11430Potassium CarbonateHCID 68532897Methyl 2-(1-tert-Butoxycarbonylpiperidin-4-yloxy)-4-hydroxybenzoate

Product 1

HCID 68535509Methyl 2-(1-tert-Butoxycarbonylpiperidin-4-yloxy)-4-(methoxymethoxy)benzoateYield 96.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl 2-(1-tert-butoxycarbonylpiperidin-4-yloxy)-4-hydroxybenzoate (9.13 g, 26.0 mmol) was dissolved in DMF. Potassium carbonate (7.19 g, 52.0 mmol) was added, followed by methoxymethyl chloride (2.51 g, 31.2 mmol), and the reaction was stirred at room temperature under a drying tube for 24 h. An additional 1.2 eq of methoxymethyl chloride was added and the reaction stirred an additional 48 h. The DMF was removed in vacuo. The residue was dissolved in ethyl acetate, washed with water, dried, and the solvent was removed in vacuo to give 9.91 g (96.2%) of a viscous oil.

Workup

  1. stirringthe reaction stirred an additional 48 h
  2. customThe DMF was removed in vacuo
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with water
  5. customdried
  6. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-88a01cbd42274191ab02e8fa7a136112
Source dataset
uspto-grants-2010_04
Patent number
US07700628B2

Reaction notes

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