Methyl 4-(benzyloxy)-2-hydroxybenzoate → Methyl 4-benzyloxy-2-(1-tert-butoxycarbonylpiperidin-4-yloxy)benzoate

HRID 644291Notes

Reaction equation

HRID 644291 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[C:11]([OH:19])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:20]([N:27]1[CH2:32][CH2:31][CH:30](O)[CH2:29][CH2:28]1)([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21]>>[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[C:11]([O:19][CH:30]2[CH2:31][CH2:32][N:27]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:28][CH2:29]2)[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 225489Methyl 4-(benzyloxy)-2-hydroxybenzoateHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylate

Product 1

HCID 68532674Methyl 4-benzyloxy-2-(1-tert-butoxycarbonylpiperidin-4-yloxy)benzoate

Procedure

Methyl 4-benzyloxy-2-(1-tert-butoxycarbonylpiperidin-4-yloxy)benzoate was prepared from methyl 4-benzyloxy-2-hydroxybenzoate and 1-Boc-4-hydroxypiperidine using a procedure similar to that described in Example 21-C. The crude material, in dichloromethane, was filtered and purified by chromatography over silica gel using a preparative high pressure chromatography apparatus, eluting with a gradient of 9:1 to 4:1 to 3:1 hexane:ethyl acetate to give 12.8 g of a white solid.

Workup

  1. filtrationThe crude material, in dichloromethane, was filtered
  2. custompurified by chromatography over silica gel using a preparative high pressure chromatography apparatus
  3. washeluting with a gradient of 9:1 to 4:1 to 3:1 hexane

Sources & evidence

ORD record
ord-046a7ee3c2684af0a9f9c320e4ed26e8
Source dataset
uspto-grants-2010_04
Patent number
US07700628B2

Reaction notes

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