1-Benzyl-4-(4-carboxyphenoxymethyl)piperidin-4-ol → 1-Benzyl-4-(4-methoxycarbonylphenoxymethyl)piperidin-4-ol

HRID 967770Notes

Reaction equation

HRID 967770 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([CH2:15][O:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]([OH:25])=[O:24])=[CH:19][CH:18]=2)([OH:14])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:26][Si](C=[N+]=[N-])(C)C.CCCCCC>CO>[CH2:1]([N:8]1[CH2:9][CH2:10][C:11]([CH2:15][O:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]([O:25][CH3:26])=[O:24])=[CH:19][CH:18]=2)([OH:14])[CH2:12][CH2:13]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 222912941-Benzyl-4-(4-carboxyphenoxymethyl)piperidin-4-olHCID 86587183Trimethylsilyldiazomethane hexane

Product 1

HCID 222912651-Benzyl-4-(4-methoxycarbonylphenoxymethyl)piperidin-4-ol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The compound (0.86 g) obtained in Step 4 was dissolved in methanol (10 mL) and to the solution was added a 2M trimethylsilyidiazomethan-hexane solution (1.3 mL). After completion of the reaction, the residue from which the solvent was removed under reduced pressure was purified by silica gel column chromatography (Chromatorex NH™) (eluent; ethyl acetate:hexane=1:19 to 1:9) to obtain the titled compound (0.8 g) as crystals.

Workup

  1. customAfter completion of the reaction
  2. customthe residue from which the solvent was removed under reduced pressure
  3. customwas purified by silica gel column chromatography (Chromatorex NH™) (eluent; ethyl acetate:hexane=1:19 to 1:9)

Sources & evidence

ORD record
ord-977f295bf3f34f6e9fe71dfc1a2dc284
Source dataset
uspto-grants-2005_10
Patent number
US06956046B2

Reaction notes

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