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Hydrochloric Acid → 5-Amino-7-tert-butyl-2,3-dihydro-3,3-dimethylbenzofuran

HRID 2290120
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HRID 2290120 반응식
Br[C:2]1[CH:3]=[C:4]([C:13]([CH3:16])([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:30])(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]>[NH2:30][C:2]1[CH:3]=[C:4]([C:13]([CH3:16])([CH3:15])[CH3:14])[C:5]2[O:9][CH2:8][C:7]([CH3:11])([CH3:10])[C:6]=2[CH:12]=1
참가 물질실험 절차출처 및 근거반응 노트

참가 물질

9

반응물 5

HCID 313Hydrochloric AcidHCID 136809Benzophenone imineHCID 634876Binap, (A+-)-HCID 107793125-Bromo-7-tert-butyl-2,3-dihydro-3,3-dimethylbenzo[b]furan2회HCID 23676156Sodium t-butoxide

생성물 1

HCID 106804065-Amino-7-tert-butyl-2,3-dihydro-3,3-dimethylbenzofuran

시약·촉매·용매 3

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 1140Toluene용매HCID 8028Tetrahydrofuran용매

실험 절차

Following general procedure D and using 5-bromo-7-t-butyl-3,3-dimethyl-2,3-dihydro-benzofuran (Compound 10, see J. Med. Chem. 1998, 41, 1124-1137; 2.0 g, 5.5 mmol), benzophenone imine (1.2 g, 6.64 mmol), sodium-tert-butoxide (0.74 g, 7.75 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.025 g, 0.026 mmol) and (S)-(-)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (0.050 g, 0.078 mmol) in 10 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 (0.95 g, 72%). 1H NMR (300 MHz, CDCl3): δ 6.49 (d, 1H, J=2.4 Hz), 6.39 (d, 1H, J=2.4 Hz), 4.17 (s, 2H), 3.38 (br s, 2H), 1.37 (s, 9H), 1.32 (s, 6H).

출처 및 근거

ORD 기록
ord-411eb68793b547c985488bb3d2cc71c6
출처 데이터셋
uspto-grants-2000_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06093838

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