Tributylstannane → 2-(3-Hydroxycyclohexyl)isoindoline-1,3-dione

HRID 2280724Notes

Reaction equation

C([SnH](CCCC)CCCC)CCC.Br[CH:15]1[CH:20]([OH:21])[CH2:19][CH2:18][CH2:17][CH:16]1[N:22]1[C:30](=[O:31])[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:23]1=[O:32].N(C(C)(C)C#N)=NC(C)(C)C#N>C1(C)C=CC=CC=1.CO>[OH:21][CH:20]1[CH2:19][CH2:18][CH2:17][CH:16]([N:22]2[C:23](=[O:32])[C:24]3[C:29](=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:30]2=[O:31])[CH2:15]1

Participants

Conditions

Temperature: 80 °C

Procedure

Tri-n-butyltin hydride (430 g, 1.48 mol) was added to a stirred solution of 2-(2-bromo-3-hydroxy-cyclohexyl)-isoindole-1,3-dione (400 g, 1.23 mol) and 2,2′-azobis(2-methylpropionitrile) (20 g) in toluene (4000 mL) and methanol (400 mL) and the reaction mixture was stirred at 80° C. for 64 h. The reaction mixture was concentrated to give the crude product. The crude product was washed with petroleum ether and ethyl acetate (1:1) to give 2-(3-hydroxy-cyclohexyl)-isoindole-1,3-dione (240 g, 0.98 mol) as a white solid. 1H NMR (CD3OD, 400 MHz): δ ppm 7.82 (m, 4H), 4.16 (m, 1H), 3.63 (m, 1H), 2.13 (m, 2H), 1.98 (d, 2H), 1.89 (m, 1H),1.68 (t, 1H), 1.46 (m, 1H),1.31 (m, 1H).

Workup

concentrationThe reaction mixture was concentrated
customto give the crude product
washThe crude product was washed with petroleum ether and ethyl acetate (1:1)

Sources & evidence

ORD record: ord-af7a7f7d828241e9adf130d520d55cbf
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09139534B2

Reaction notes

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