Hydrochloric Acid → 5-Amino-3,3-dimethyl-7-isopropyl-2,3-dihydrobenzofuran

HRID 2290119Notes

Reaction equation

HRID 2290119 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:13]([CH3:15])[CH3:14])[C:5]2[O:9][CH2:8][C:7]([CH3:11])([CH3:10])[C:6]=2[CH:12]=1.C(=[NH:29])(C1C=CC=CC=1)C1C=CC=CC=1.CC(C)([O-])C.[Na+].C1C=CC(P(C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl>C1(C)C=CC=CC=1.O1CCCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[NH2:29][C:2]1[CH:3]=[C:4]([CH:13]([CH3:15])[CH3:14])[C:5]2[O:9][CH2:8][C:7]([CH3:11])([CH3:10])[C:6]=2[CH:12]=1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 136809Benzophenone imineHCID 634876Binap, (A+-)-HCID 154540775-Bromo-3,3-dimethyl-7-isopropyl-2,3-dihydro-benzofuran2×HCID 23676156Sodium t-butoxide

Product 1

HCID 154540815-Amino-3,3-dimethyl-7-isopropyl-2,3-dihydrobenzofuran

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Following general procedure D and using 5-bromo-3,3-dimethyl-7-isopropyl-2,3-dihydro-benzofuran (Compound 8, 0.268 g, 1 mmol), benzophenone imine (0.199 g, 1.1 mmol), sodium-tert-butoxide (0.134 g, 1.4 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.020 g, 0.021 mmol) and (S)-(-)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (0.040 g, 0.064 mmol) in 5 mL of anhydrous toluene, followed by hydrolysis of the intermediary imine with 2M hydrochloric acid in tetrahydrofuran, the title compound was obtained as an oil (0.131 g, 69%). 1H NMR (300 MHz, CDCl3): δ 6.39 (d, 1H, J=2.3 Hz), 6.33 (d, 1H, J=2.3 Hz), 4.15 (s, 2H), 3.32 (br s, 2H), 3.03 (heptet, 1H, J=6.9 Hz), 1.28 (s, 6H), 1.22 (d, 6H, J=6.9 Hz).

Sources & evidence

ORD record
ord-bc7284fe00d74fcc85b62071a7656885
Source dataset
uspto-grants-2000_07
Patent number
US06093838

Reaction notes

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