Acetic Acid → 1-(3-(4-Bromophenyl)propyl)pyrrolidine

HRID 1916579노트

반응식

HRID 1916579 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH:10]=O)=[CH:4][CH:3]=1.[NH:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1.C(O)(=O)C.[BH3-]C#N.[Na+]>CO.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][N:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)=[CH:4][CH:3]=1

참가 물질

7

반응물 4

HCID 176Acetic AcidHCID 31268PyrrolidineHCID 5003444Sodium cyanoborohydrideHCID 114812883-(4-Bromophenyl)propanal

생성물 1

HCID 248235691-(3-(4-Bromophenyl)propyl)pyrrolidine

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매

실험 절차

A solution of 1.03 g (4.82 mmol) 3-(4-bromo-phenyl)-propionaldehyde and 0.41 mL (4.82 mmol) pyrrolidine in 50 mL MeOH is adjusted to pH 4-5 with glacial acetic acid. Then 400 mg (6.05 mmol) NaBH3CN are added batchwise and the reaction is stirred for 3 days at RT. The reaction solution is diluted with 30 mL water and the aqueous phase is extracted with 50 mL EtOAc. The organic phase is dried over Na2SO4 and the solvent is eliminated i.vac. Further purification is carried out by column chromatography on silica gel (EtOAc/MeOH/NH3 9:1:0.1).

후처리

  1. extractionthe aqueous phase is extracted with 50 mL EtOAc
  2. dry with materialThe organic phase is dried over Na2SO4
  3. customFurther purification

출처 및 근거

ORD 기록
ord-e5414667fb264f29a7e213dbd0fcc68e
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08618132B2

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