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

HRID 1696282노트

반응식

HRID 1696282 반응식
[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

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 887Methanol용매HCID 1049Pyridine용매HCID 6386tert-Butanol용매

실험 절차

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)

후처리

  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

출처 및 근거

ORD 기록
ord-473d86c96a4f41608217558a6351876b
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08163766B2

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