Tributylstannane → (1S,3R)-2-(3-hydroxy-cyclohexyl)-isoindole-1,3-dione
Reaction equation
C([SnH](CCCC)CCCC)CCC.Br[C@@H:15]1[C@@H:20]([OH:21])[CH2:19][CH2:18][CH2:17][C@H: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]>C1(C)C=CC=CC=1.CO.N(C(C)(C)C#N)=NC(C)(C)C#N>[OH:21][C@@H:20]1[CH2:19][CH2:18][CH2:17][C@H: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]1Participants
6
Reactant 2
Product 1
Reagents, catalysts & solvents 3
Procedure
Tributyltin hydride (1.99 ml, 7.40 mmol) and 2,2′-azobis(isobutyronitrile) (8 mg) were added to a solution of 2-[(1R, 2S, 3S)-2-bromo-3-hydroxycyclohexyl]-1H-isoindole-1,3(2H)-dione (2.0 g, 6.17 mmol) in a mixture of toluene (40 ml) and methanol (4 ml) at room temperature, and the resulting mixture was refluxed for 3 hours. Tributyltin hydride (1.99 ml, 7.40 mmol) and 2,2′-azobis(isobutyronitrile) (8 mg) were further added thereto, and the resulting mixture was refluxed for 1 hour. The reaction solution was concentrated and the resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate=2/1) to obtain cis-2-(3-hydroxycyclohexyl)-1H-isoindole-1,3(2H)-dione (1.33 g, 88%).
Workup
- temperaturethe resulting mixture was refluxed for 3 hours
- temperaturethe resulting mixture was refluxed for 1 hour
- concentrationThe reaction solution was concentrated
- customthe resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate=2/1)
Sources & evidence
- ORD record
- ord-b4b44fe6e1ee4080806b2b541db845e7
- Source dataset
- uspto-grants-2007_04
- Patent number
- US07199147B2
Reaction notes
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