Cyanomethylenetributylphosphorane → Methyl 1-({4-[({4-[(4-methoxybenzyl)oxy]-1,2-benzisoxazol-3-yl]oxy)methyl}piperidin-1-yl}methyl)-cyclopentanecarboxylate

HRID 2410338Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:6]([CH2:7][O:8][C:9]2[C:14]3[C:15]([OH:18])=[N:16][O:17][C:13]=3[CH:12]=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.O[CH2:22][CH:23]1[CH2:28][CH2:27][N:26]([CH2:29][C:30]2([C:35]([O:37][CH3:38])=[O:36])[CH2:34][CH2:33][CH2:32][CH2:31]2)[CH2:25][CH2:24]1.C(C=P(CCCC)(CCCC)CCCC)#N>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][O:8][C:9]2[C:14]3[C:15]([O:18][CH2:22][CH:23]4[CH2:28][CH2:27][N:26]([CH2:29][C:30]5([C:35]([O:37][CH3:38])=[O:36])[CH2:31][CH2:32][CH2:33][CH2:34]5)[CH2:25][CH2:24]4)=[N:16][O:17][C:13]=3[CH:12]=[CH:11][CH:10]=2)=[CH:19][CH:20]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 4-[(4-methoxybenzyl)oxy]-1,2-benzisoxazol-3-ol (100 mg, 0.369 mmol, EXAMPLE 9, step 2) and methyl 1-{[4-(hydroxymethyl)piperidin-1-yl]methyl}cyclopentanecarboxylate (141 mg, 0.553 mmol, EXAMPLE 9, step 3) in toluene (2.5 mL) was added cyanomethylenetributylphosphorane (178 mg, 0.737 mmol) at room temperature. The reaction mixture was heated at 100° C. for 20 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 5:2 to 3:2) to give 116 mg (62%) of the title compound as a white solid.

Workup

temperatureAfter cooling
concentrationthe mixture was concentrated in vacuo
customto give a dark brown oil
customThe residual oil was purified by silica gel column chromatography (hexane/ethyl acetate 5:2 to 3:2)

Sources & evidence

ORD record: ord-46ee8fad73db4523b163d800aa29088b
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08816090B2

Reaction notes

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