Ammonium formate → HCID 10464367, 화합물

HRID 965469노트

반응식

HRID 965469 반응식
C([N:8]1[CH2:12][CH2:11][C@@H:10]([C@@H:13]([NH:15][CH3:16])[CH3:14])[CH2:9]1)C1C=CC=CC=1.C([O-])=O.[NH4+]>CO.[OH-].[OH-].[Pd+2].C(Cl)Cl.CO>[CH3:16][NH:15][C@H:13]([C@@H:10]1[CH2:11][CH2:12][NH:8][CH2:9]1)[CH3:14]

참가 물질

6

반응물 2

HCID 2723923Ammonium formateHCID 9904942HCID 9904942, 화합물

생성물 1

HCID 10464367HCID 10464367, 화합물

시약·촉매·용매 3

HCID 9942167Palladium hydroxide촉매HCID 887Methanol용매HCID 21226129Dichloromethane methanol용매

실험 절차

(R,S)-1-benzyl-3-[1'-(methylamino)ethyl]pyrrolidine (0.51 g of crude product) is dissolved in MeOH (10 ml) under a N2 atmosphere, Pearlman's catalyst and ammonium formate (0.89 g, 14.11 mmol) are then added. The reaction mixture is refluxed for 12 hours. The reaction mixture is then diluted with CH2Cl2 :MeOH (1:1) and filtered through a celite pad. The filtrate is washed with 15% aqueous NaOH:brine (1:1) and the aqueous layer is back extracted with CH2Cl2 (2×). The combined organic layers are dried over MgSO4, filtered and concentrated under a stream of N2 to give crude (R,S)-3-[1'-(methylamino)ethyl]pyrrolidine: 1H NMR (300 MHz, CDCl3) δ 1.05 (d, J is 6.3 Hz, 3H), 1.43 (ddd, J is 17, 12, 9 Hz, 1H), 1.87 (m, 1H), 2.02 (dd, J is 16, 8 Hz, 1H), 2.38 (s, 3H), 2.41 (m, 1H), 2.61 (broad s, 2H), 2.65 (dd, J is 11, 8 Hz, 1H), 2.91-3.00 (m, 2H), 3.13 (dd, J is 11, 8 Hz, 1H). This material is suitable for use in various reactions including but not limited to the synthesis of quinolones.

후처리

  1. temperatureThe reaction mixture is refluxed for 12 hours
  2. filtrationfiltered through a celite pad
  3. washThe filtrate is washed with 15% aqueous NaOH:brine (1:1)
  4. extractionthe aqueous layer is back extracted with CH2Cl2 (2×)
  5. dry with materialThe combined organic layers are dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under a stream of N2

출처 및 근거

ORD 기록
ord-73452398068d447c831ac7386abb3947
출처 데이터셋
uspto-grants-1998_06
특허 번호
US05773610

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