2-Fluoropyridine → Benzyl 1-(pyridin-2-yl)piperidine-3-carboxylate

HRID 253099ノート

反応式

HRID 253099 の反応式
[NH:1]1[CH2:6][CH2:5][CH2:4][CH:3]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[CH2:2]1.CCN(C(C)C)C(C)C.F[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=1.C([O-])([O-])=O.[Na+].[Na+]>CO.N1C=CC=CC=1.C(O)(C)(C)C>[N:28]1[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=1[N:1]1[CH2:6][CH2:5][CH2:4][CH:3]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[CH2:2]1

参加物

8

反応物 4

HCID 97462-FluoropyridineHCID 10340Sodium CarbonateHCID 81531DiisopropylethylamineHCID 13419237Benzyl piperidine-3-carboxylate

生成物 1

HCID 66845119Benzyl 1-(pyridin-2-yl)piperidine-3-carboxylate

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 1049Pyridine溶媒HCID 6386tert-Butanol溶媒

実験手順

Pure benzyl piperidine-3-carboxylate (170 mg, 0.776 mmol; Example 31) was placed in a microwave tube. DIPEA (0.50 mL), tert-BuOH (1.5 mL) and 2-fluoropyridine (Aldrich, 0.40 mL) were added to the tube via syringes before the tube was subjected to microwave irradiation at 180° C. for 20 min. LC/MS showed partial conversion to the desired pyridine derivative. The tube was subjected to further microwave irradiation at 220° C. for 20 min and then it was allowed to cool to room temperature. The volatiles were removed by rotary evaporation to provide 229 mg of crude oil which was dissolved in MeOH (8.0 mL) and then subjected to reverse phase HPLC. The pure fractions were poured into Na2CO3 (10%, 75 mL) and extracted with EtOAc (3×50 mL), washed with brine (sat, 150 mL), dried with sodium sulfate, filtered and concentrated to provide 90 mg of benzyl 1-(pyridin-2-yl)piperidine-3-carboxylate. MS m/z: 297 (M+1)

後処理

  1. customirradiation at 180° C. for 20 min
  2. customThe tube was subjected to further microwave irradiation at 220° C. for 20 min
  3. customThe volatiles were removed by rotary evaporation
  4. customto provide 229 mg of crude oil which
  5. extractionextracted with EtOAc (3×50 mL)
  6. washwashed with brine (sat, 150 mL)
  7. dry with materialdried with sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

出典と根拠

ORDレコード
ord-a2cb59c59406492ebb4d10a099813c84
出典データセット
uspto-grants-2011_01
特許番号
US07872009B2

反応ノート

読み込み中…