Trifluoroacetic acid → HCID 19925593、化合物

HRID 1647507ノート

反応式

HRID 1647507 の反応式
C(OC([NH:8][C:9]1[CH:10]=[C:11]([C:15]2([OH:21])[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[CH:12]=[CH:13][CH:14]=1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[NH2:8][C:9]1[CH:10]=[C:11]([C:15]2([OH:21])[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[CH:12]=[CH:13][CH:14]=1

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 19925596HCID 19925596、化合物

生成物 1

HCID 19925593HCID 19925593、化合物収率 77%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

To an ice-cooled solution of 4-(3-t-butyloxycarbonylaminophenyl)-4-hydroxytetrahydropyran (2.0 g, 6.8 mmol), prepared as in step 2, in dichloromethane (14 mL) was added trifluoroacetic acid (14, mL). The resulting solution was stirred for 0.25 hours at 0° C. and 1 hour at ambient temperature. The volatiles were removed in vacuo and the resulting solution was basified with saturated aqueous potassium carbonate. The resulting mixture was diluted with dichloromethane and the layers separated. The aqueous layer was extracted (4×, dichloromethane). The combined organic layers were dried (MgSO4), and concentrated in vacuo to provide a solid. Trituration with hexanes provided 4-(3-aminophenyl)-4-hydroxytetrahydropyran as a colorless solid (1.01 g, 77%). mp 154°-155° C. 1H NMR (300 MHz, CDCl3) δ7.17 (1H, dt, J=7.5, 1 Hz), 6.84-6.88 (2H, m), 6.62 (1H, br d, J=7.5 Hz), 3.93 (2H, td, J=12, 12, 2.5 Hz), 3.84 (2H, ddd, J=12, 5, 1.5 Hz), 2.05-32 (4H, m). MS m/e 193 (M+NH4 --H2O)+, 211 (M+NH4)+.

後処理

  1. customThe volatiles were removed in vacuo
  2. additionThe resulting mixture was diluted with dichloromethane
  3. customthe layers separated
  4. extractionThe aqueous layer was extracted (4×, dichloromethane)
  5. dry with materialThe combined organic layers were dried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customto provide a solid

出典と根拠

ORDレコード
ord-aca13c46b86c4fa0ab69e3d54f7ff314
出典データセット
uspto-grants-1995_07
特許番号
US05432194

反応ノート

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