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

HRID 532222Notes

Reaction equation

HRID 532222 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.[C:32]1(=O)CCCCC1>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][CH2:32][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 7967CyclohexanoneHCID 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 715722345-(5-(3,5-Dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-1H-spiro[benzo[c][1,2]oxaborole-3,1'-cyclohexan]-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 cyclohexanone to replace 3-pentanone. It was obtained as a white solid. 1H NMR (300 MHz, DMSO-d6): δ 9.22 (s, 1H), 7.82-7.61 (m, 6H), 4.47-4.27 (m, 2H), 1.68-0.84 (m, 10H). MS: m/z=484 [M+1]+.

Workup

  1. customIt was obtained as a white solid

Sources & evidence

ORD record
ord-05397dd53cb248b380931035c90bf436
Source dataset
uspto-grants-2014_10
Patent number
US08853186B2

Reaction notes

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