Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate → tert-Butyl 4-({[4-(2,2,2-trifluoroethoxy)-1,2-benzisoxazol-3-yl]oxy}methyl)piperidine-1-carboxylate

HRID 2410323Notes

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]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21][CH2:20]1.C(P(=C(C(OC)=O)C(OC)=O)(CCCC)CCCC)CCC>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]([C:25]([O:27][C:28]([CH3:29])([CH3:31])[CH3:30])=[O:26])[CH2:21][CH2:20]3)=[N:12][O:13][C:9]=2[CH:8]=[CH:7][CH:6]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 4-(2,2,2-trifluoroethoxy)-1,2-benzisoxazol-3-ol (0.12 g, 0.50 mmol, EXAMPLE 1, step 2), tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate (0.13 g, 0.60 mmol), and dimethyl (tributylphosphoranylidene)malonate (0.32 g, 1.0 mmol, J. Org. Chem. 2003, 68, 1597-1600) in toluene (0.5 mL) was stirred at 80° C. for 16 h. The mixture was purified by silica gel column chromatography (hexane/ethyl acetate 4:1) to give 0.14 g (65%) of the title compound as a white solid.

Workup

customThe mixture was purified by silica gel column chromatography (hexane/ethyl acetate 4:1)

Sources & evidence

ORD record: ord-0fb377e5539143439ec3b900f8dd8056
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08816090B2

Reaction notes

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