反応式
[C:1]12([NH2:11])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.Br[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.CC(C)([O-])C.[Na+].CCOCC>C1(C)C=CC=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].C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:1]12([NH:11][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:8][CH:7]3[CH2:6][CH:5]([CH2:4][CH:3]([CH2:9]3)[CH2:2]1)[CH2:10]2参加物
実験手順
A mixture of Pd(dba)2 (0.259 g, 0.450 mmol) and (±)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthalene (0.417 g, 0.670 mmol) in toluene (40 mL) was stirred for 30 min at room temperature before adding 1-adamantylamine (2.269 g, 15.0 mmol), bromobenzene (1.60 mL, 15.2 mmol) and sodium tert-butoxide (2.02 g, 21.0 mmol). The reaction solution was stirred for 24 h at 100° C. After cooling the reaction mixture to room temperature, Et2O (50 mL) was added. The reaction mixture was filtered through a pad of celite and was concentrated. Flash column chromatography (silicagel, 7:1 hexanes/EtOAc) afforded the desired product (2.239 g, 65.7%) as a pale yellow solid. 1H NMR (300 MHz, CDCl3) δ 7.18 (t, J=7.6 Hz, 2H), 6.83 (m, 3H), 3.26 (br. s, 1H), 2.14 (m, 3H), 1.91 (m, 6H), 1.71 (m, 6H); 13C NMR (75 MHz, CDCl3) δ 146.3, 129.0, 119.4, 119.3, 52.5, 43.8, 36.8, 30.0. HRMS-ESI (m/z): [M+H]+ calcd for C16H21N, 228.1747. found, 228.1756.
後処理
- stirringThe reaction solution was stirred for 24 h at 100° C
- temperatureAfter cooling the reaction mixture to room temperature
- filtrationThe reaction mixture was filtered through a pad of celite
- concentrationwas concentrated
出典と根拠
- ORDレコード
- ord-1d7816f6841345f49a67baf64ce4e240
- 出典データセット
- uspto-grants-2013_09
- 特許番号
- US08530687B2
関連ノート
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