4-(Aminomethyl)piperidine → (R)-alpha-Amino-N-methyl-N-[(2'-nitro)[1,1'-biphenyl]-4-yl]-benzenebutanamide

HRID 1923

反応式

HRID 1923 の反応式
C1C2C(COC([NH:18][C@H:19]([CH2:39][CH2:40][C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[C:20]([N:22]([CH3:38])[C:23]3[CH:28]=[CH:27][C:26]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=4[N+:35]([O-:37])=[O:36])=[CH:25][CH:24]=3)=[O:21])=O)C3C(=CC=CC=3)C=2C=CC=1.NCC1CCNCC1>C(Cl)Cl>[NH2:18][C@H:19]([CH2:39][CH2:40][C:41]1[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1)[C:20]([N:22]([CH3:38])[C:23]1[CH:28]=[CH:27][C:26]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[N+:35]([O-:37])=[O:36])=[CH:25][CH:24]=1)=[O:21]

参加物

4

反応物 2

HCID 235274-(Aminomethyl)piperidineHCID 22883387(R)-alpha-[N-(9-Fluorenylmethoxycarbonyl)amino]-N-methyl-N-[(2'-nitro)[1,1'-biphenyl]-4-yl]-benzenebutanamide

生成物 1

HCID 22883384(R)-alpha-Amino-N-methyl-N-[(2'-nitro)[1,1'-biphenyl]-4-yl]-benzenebutanamide

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

The FMOC amide from Step F (1.15 g; 1.88 mmol) was dissolved in methylene chloride (10 ml) and 4-(aminomethyl)piperidine (1 ml) added. The reaction mixture was stirred at room temperature. The reaction mixture was stirred for 15 minutes and then quenched by adding water. The methylene chloride phase was separated, dried over ahnydrous potassium carbonate powder, filtered and evaprated under reduced pressure to afford an orange-yellow oil. The oil was chromatographed on silica gel using an eluant of ethyl acetate and methanol (9:1 v/v). A pale yellow oil (517 mg; 70.6%) was isolated of the amine. FAB-MS:- calculated for C23H23N3 O3 389.2 found 389.9 (M).

後処理

  1. stirringThe reaction mixture was stirred for 15 minutes
  2. customquenched
  3. additionby adding water
  4. customThe methylene chloride phase was separated
  5. dry with materialdried over ahnydrous potassium carbonate powder
  6. filtrationfiltered
  7. customto afford an orange-yellow oil
  8. customThe oil was chromatographed on silica gel using an eluant of ethyl acetate and methanol (9:1 v/v)

出典と根拠

ORDレコード
ord-4973b5510ea745408780d7b531a293b6
出典データセット
uspto-grants-1998_03
特許番号
US05726319

関連ノート

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