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

HRID 1923노트

반응식

HRID 1923 반응식
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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-4973b5510ea745408780d7b531a293b6
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05726319

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