Pyrrolidine → HCID 62177350、化合物

HRID 1916620ノート

反応式

HRID 1916620 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

HCID 62177350HCID 62177350、化合物

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-33ef7ad9873d47acb3ee82c9b720e312
出典データセット
uspto-grants-2013_12
特許番号
US08618132B2

反応ノート

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