Cyclopentanone → 5-(5-(3,5-Dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-1H-spiro[benzo[c][1,2]oxaborole-3,1'-cyclopentan]-1-ol

HRID 1750841Notes

Reaction equation

HRID 1750841 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:28]([F:31])([F:30])[F:29])[O:13][N:12]=[C:11]([C:14]3[CH:27]=[CH:26][C:17]4[B:18]([OH:25])[O:19][C:20]([CH2:23][CH3:24])([CH2:21][CH3:22])[C:16]=4[CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.C1(=O)CCCC1>CCC(=O)CC>[Cl:8][C:6]1[CH:5]=[C:4]([C:9]2([C:28]([F:29])([F:31])[F:30])[O:13][N:12]=[C:11]([C:14]3[CH:27]=[CH:26][C:17]4[B:18]([OH:25])[O:19][C:20]5([CH2:23][CH2:24][CH2:22][CH2:21]5)[C:16]=4[CH:15]=3)[CH2:10]2)[CH:3]=[C:2]([Cl:1])[CH:7]=1

Participants

4

Reactant 2

HCID 8452CyclopentanoneHCID 715721205-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-3,3-diethyl-benzo[c][1,2]oxaborol-1(3H)-ol

Product 1

HCID 715722335-(5-(3,5-Dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-1H-spiro[benzo[c][1,2]oxaborole-3,1'-cyclopentan]-1-ol

Reagents, catalysts & solvents 1

HCID 7288Ethyl ketoneSolvent

Procedure

The title compound was prepared by using the same method as described for 5-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-3,3-diethyl-benzo[c][1,2]oxaborol-1(3H)-ol with cyclopentanone to replace 3-pentanone. It was obtained as a white solid. 1H NMR (300 MHz, DMSO-d6): δ 9.20 (s, 1 H), 7.80 (t, J=1.8 Hz, 1 H), 7.72 (s, 3 H), 7.61 (d, J=1.5 Hz, 2 H), 4.44 (d, J=18.3 Hz, 1 H), 4.31 (d, J=18.3 Hz, 1 H), 2.11-1.71 (m, 8 H) ppm.

Workup

  1. customIt was obtained as a white solid

Sources & evidence

ORD record
ord-035011bf93944975b5c4f0d8c6a2d5c0
Source dataset
uspto-grants-2015_10
Patent number
US09156860B2

Reaction notes

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