Methyl 4-{[4-(hydroxymethyl)piperidin-1-yl]methyl}tetrahydro-2H-pyran-4-carboxylate → HCID 69317159, compound

HRID 2410321Notes

Reaction equation

HRID 2410321 reaction equation
[F:1][C:2]([F:16])([F:15])[CH2:3][O:4][C:5]1[C:10]2[C:11]([OH:14])=[N:12][O:13][C:9]=2[CH:8]=[CH:7][CH:6]=1.O[CH2:18][CH:19]1[CH2:24][CH2:23][N:22]([CH2:25][C:26]2([C:32]([O:34][CH3:35])=[O:33])[CH2:31][CH2:30][O:29][CH2:28][CH2:27]2)[CH2:21][CH2:20]1.C(CP(CCCC)(CCCC)CCCC)#N>C1(C)C=CC=CC=1>[F:16][C:2]([F:1])([F:15])[CH2:3][O:4][C:5]1[C:10]2[C:11]([O:14][CH2:18][CH:19]3[CH2:24][CH2:23][N:22]([CH2:25][C:26]4([C:32]([O:34][CH3:35])=[O:33])[CH2:31][CH2:30][O:29][CH2:28][CH2:27]4)[CH2:21][CH2:20]3)=[N:12][O:13][C:9]=2[CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 69316474Methyl 4-{[4-(hydroxymethyl)piperidin-1-yl]methyl}tetrahydro-2H-pyran-4-carboxylateHCID 178454897HCID 178454897, compoundHCID 178518987HCID 178518987, compound

Product 1

HCID 69317159HCID 69317159, compoundYield 51.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-(2,2,2-trifluoroethoxy)-1,2-benzisoxazol-3-ol (230 mg, 1 mmol, EXAMPLE 1, step 2), methyl 4-{[4-(hydroxymethyl)piperidin-1-yl]methyl}tetrahydro-2H-pyran-4-carboxylate (270 mg, 1 mmol, EXAMPLE 1, step 4), and cyanomethyltributylphosphorane (400 mg, 1.5 mmol) in toluene (1.0 mL) was stirred at 100° C. for 16 h. After cooling, the mixture was concentrated in vacuo to give a dark brown oil. The residual oil was purified by silica gel column chromatography (hexane/ethyl acetate 2:1) to give 250 mg (51%) of the title compound as a white solid.

Workup

  1. temperatureAfter cooling
  2. concentrationthe mixture was concentrated in vacuo
  3. customto give a dark brown oil
  4. customThe residual oil was purified by silica gel column chromatography (hexane/ethyl acetate 2:1)

Sources & evidence

ORD record
ord-aeee9311d665472482aefa1dbee94907
Source dataset
uspto-grants-2014_08
Patent number
US08816090B2

Reaction notes

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