Pyrrolidine → HCID 62177350, 화합물

HRID 1916620노트

반응식

HRID 1916620 반응식
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:6][NH:7][C:8]1[CH:15]=[CH:14][C:11]([CH:12]=O)=[CH:10][C:9]=1[N+:16]([O-:18])=[O:17].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C([O-])(O)=O.[Na+]>C1COCC1.C(O)(=O)C>[CH3:6][NH:7][C:8]1[CH:15]=[CH:14][C:11]([CH2:12][N:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)=[CH:10][C:9]=1[N+:16]([O-:18])=[O:17]

참가 물질

7

반응물 4

HCID 31268PyrrolidineHCID 516892Sodium BicarbonateHCID 38542614-(methylamino)-3-nitrobenzaldehydeHCID 5049666Sodium triacetoxyborohydride

생성물 1

HCID 62177350HCID 62177350, 화합물

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 8028Tetrahydrofuran용매

실험 절차

5.55 g (78.0 mmol) pyrrolidine are added to a solution of 4.70 g (26.1 mmol) 4-methylamino-3-nitro-benzaldehyde in 100 mL THF and the reaction mixture is acidified with glacial acetic acid. 6.36 g (30.0 mmol) NaBH(OAc)3 are added and the reaction mixture is stirred overnight at RT. The mixture is combined with saturated NaHCO3 solution and the aqueous phase is extracted twice with EtOAc. The combined organic extracts are washed with 200 mL semisaturated NaHCO3 solution and dried over MgSO4. The solvent is eliminated i.vac. and further purification is carried out by column chromatography on silica gel (gradient: DCM to DCM/MeOH 9:1).

후처리

  1. extractionthe aqueous phase is extracted twice with EtOAc
  2. washThe combined organic extracts are washed with 200 mL
  3. dry with materialdried over MgSO4
  4. customand further purification

출처 및 근거

ORD 기록
ord-33ef7ad9873d47acb3ee82c9b720e312
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08618132B2

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