Hydrochloric Acid → (+/-)-1-[7-(2,3-Dimethylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methanamine

HRID 2116210ノート

反応式

HRID 2116210 の反応式
CC1C=CC(S(O[CH2:12][CH:13]2[CH2:17][C:16]3[CH:18]=[CH:19][CH:20]=[C:21]([C:22]4[CH:27]=[CH:26][CH:25]=[C:24]([CH3:28])[C:23]=4[CH3:29])[C:15]=3[O:14]2)(=O)=O)=CC=1.[N-:30]=[N+]=[N-].[Na+].N(CC1CC2C=CCC(C3C=CC=C(Cl)C=3Cl)(N)C=2O1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Cl>O1CCCC1.C(O)(C)C>[CH3:29][C:23]1[C:24]([CH3:28])=[CH:25][CH:26]=[CH:27][C:22]=1[C:21]1[C:15]2[O:14][CH:13]([CH2:12][NH2:30])[CH2:17][C:16]=2[CH:18]=[CH:19][CH:20]=1

参加物

8

反応物 5

HCID 313Hydrochloric AcidHCID 11776TriphenylphosphineHCID 33557Sodium AzideHCID 86599147(+/-)-[7-(2,3-Dimethylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl 4-methylbenzenesulfonateHCID 86599249(+/-)-2-(Azidomethyl)-7-(2,3-dichlorophenyl)-2,3-dihydro-1-benzofuran-7 amine2 回

生成物 1

HCID 11357234(+/-)-1-[7-(2,3-Dimethylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methanamine収率 54%

試薬・触媒・溶媒 2

HCID 3776Isopropanol溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

Treatment of (±)-(7-bromo-2,3-dihydro-1-benzofuran-2-yl)methyl 4-methylbenzenesulfonate (0.50 g, 1.305 mmol) with (2,3-dimethyl-phenyl)boronic acid (0.294 g, 1.96 mmol), dichlorobis(tri-o-tolylphosphine)-palladium(II) (0.041 g, 0.052 mmol), and potassium carbonate (0.41 g, 3.25 mmol) generally according to the procedure described for Intermediate 37 provided 0.335 g (62%) of (±)-[7-(2,3-dimethylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl 4-methylbenzenesulfonate. Treatment of (±)-[7-(2,3-dimethylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl 4-methylbenzenesulfonate with sodium azide (0.134 g, 2.06 mmol) generally according to the procedure described for Intermediate 98 afforded (±)-2-(azidomethyl)-7-(2,3-dichlorophenyl)-2,3-dihydro-1-benzofuran-7 amine. To a solution of (±)-2-(azidomethyl)-7-(2,3-dichlorophenyl)-2,3-dihydro-1-benzofuran-7 amine (0.135 g, 1.483 mmol) in tetrahydrofuran (5 mL) was added polymer supported triphenyl phosphine (0.152 g, 0.58 mmol) and the reaction mixture was allowed to stir at room temperature for 12 h. The reaction mixture was filtered (celite) and the solvent removed in vacuo to provide a colorless oil. The oil was re-dissolved in isopropanol (3 mL) and hydrogen chloride (1.0 N in diethyl ether, 10.0 mL) was added. The resulting precipitate was filtered, washed (diethyl ether), and dried to afford 0.075 g (54%) of (±)-1-[7-(2,3-dimethylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methanamine as a white solid, hydrochloride salt. mp >225° C.:

後処理

  1. filtrationThe reaction mixture was filtered (celite)
  2. customthe solvent removed in vacuo
  3. customto provide a colorless oil
  4. filtrationThe resulting precipitate was filtered
  5. washwashed (diethyl ether)
  6. customdried

出典と根拠

ORDレコード
ord-815805dda20c443da066224276166613
出典データセット
uspto-grants-2008_10
特許番号
US07435837B2

反応ノート

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