Methyl 4-{[4-(2-{[4-(benzyloxy)-1,2-benzisoxazol-3-yl]oxy}ethyl)piperidin-1-yl]methyl}tetrahydro-2H-pyran-4-carboxylate → Methyl 4-[(4-{2-[(4-hydroxy-1,2-benzisoxazol-3-yl)oxy]ethyl}piperidin-1-yl)methyl]tetrahydro-2H-pyran-4-carboxylate

HRID 2410330Notes

Reaction equation

HRID 2410330 reaction equation
C([O:8][C:9]1[C:14]2[C:15]([O:18][CH2:19][CH2:20][CH:21]3[CH2:26][CH2:25][N:24]([CH2:27][C:28]4([C:34]([O:36][CH3:37])=[O:35])[CH2:33][CH2:32][O:31][CH2:30][CH2:29]4)[CH2:23][CH2:22]3)=[N:16][O:17][C:13]=2[CH:12]=[CH:11][CH:10]=1)C1C=CC=CC=1>O1CCCC1.CO.[Pd]>[OH:8][C:9]1[C:14]2[C:15]([O:18][CH2:19][CH2:20][CH:21]3[CH2:26][CH2:25][N:24]([CH2:27][C:28]4([C:34]([O:36][CH3:37])=[O:35])[CH2:33][CH2:32][O:31][CH2:30][CH2:29]4)[CH2:23][CH2:22]3)=[N:16][O:17][C:13]=2[CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 1

HCID 69317575Methyl 4-{[4-(2-{[4-(benzyloxy)-1,2-benzisoxazol-3-yl]oxy}ethyl)piperidin-1-yl]methyl}tetrahydro-2H-pyran-4-carboxylate

Product 1

HCID 136367381Methyl 4-[(4-{2-[(4-hydroxy-1,2-benzisoxazol-3-yl)oxy]ethyl}piperidin-1-yl)methyl]tetrahydro-2H-pyran-4-carboxylateYield 83.4%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl 4-{[4-(2-{[4-(benzyloxy)-1,2-benzisoxazol-3-yl]oxy}ethyl)piperidin-1-yl]-methyl}tetrahydro-2H-pyran-4-carboxylate (3.2 g, 6.3 mmol, EXAMPLE 7, step 5) and 10% Pd—C (0.30 g) in tetrahydrofuran (20 mL) and methanol (40 mL) was stirred at room temperature for 10 min under hydrogen atmosphere. The mixture was filtered through a pad of celite and the filtrate was concentrated in vacuo to give an oil. The residual oil was purified by silica gel column chromatography (hexane/ethyl acetate 3:1 to 3:2) to give 2.2 g (83%) of the title compound as a pale yellow solid.

Workup

  1. filtrationThe mixture was filtered through a pad of celite
  2. concentrationthe filtrate was concentrated in vacuo
  3. customto give an oil
  4. customThe residual oil was purified by silica gel column chromatography (hexane/ethyl acetate 3:1 to 3:2)

Sources & evidence

ORD record
ord-c78cbe56f271420b90e9e3ed678c8700
Source dataset
uspto-grants-2014_08
Patent number
US08816090B2

Reaction notes

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