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

HRID 1916579ノート

反応式

HRID 1916579 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-e5414667fb264f29a7e213dbd0fcc68e
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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