Diazald → 2-benzyl 3-methyl (2S,3S,5S)-1-benzyl-5-methoxypiperidine-2,3-dicarboxylate

HRID 61471

반응식

HRID 61471 반응식
[N+](=[CH2:3])=[N-].CC1C=CC(S(N(N=O)C)(=O)=O)=CC=1.[CH2:18]([N:25]1[CH2:30][C@@H:29]([OH:31])[CH2:28][C@H:27]([C:32]([O:34][CH3:35])=[O:33])[C@H:26]1[C:36]([O:38][CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)=[O:37])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CCOCC>[CH2:18]([N:25]1[CH2:30][C@@H:29]([O:31][CH3:3])[CH2:28][C@H:27]([C:32]([O:34][CH3:35])=[O:33])[C@H:26]1[C:36]([O:38][CH2:39][C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1)=[O:37])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

참가 물질

5

반응물 3

HCID 6628DiazaldHCID 9550DiazomethaneHCID 866214902-benzyl 3-methyl(2S,3S,5S)-1-benzyl-5-hydroxypiperidine-2,3-dicarboxylate

생성물 1

HCID 1317319302-benzyl 3-methyl (2S,3S,5S)-1-benzyl-5-methoxypiperidine-2,3-dicarboxylate수율 3.2%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매2회

실험 절차

Diazomethane was generated (from 5 g of Diazald) and distilled together with ether into a mixture of 2-benzyl 3-methyl(2S,3S,5S)-1-benzyl-5-hydroxypiperidine-2,3-dicarboxylate (0.60 g, 0.0016 mol) and around 1 g of silica gel in 10 mL of ether. After distillation, the mixture was stirred at rt overnight. The mixture was diluted with methylene chloride, filtered to remove silica gel. The filtration was concentrated to dry and the resulting residue was applied on column, eluting with 0 to 40% EtOAc in Hexane, to yield the methyl ether compound (20 mg, 3.2%). MS (ESI): (M+H)+=398.1.

후처리

  1. distillationAfter distillation
  2. additionThe mixture was diluted with methylene chloride
  3. filtrationfiltered
  4. customto remove silica gel
  5. filtrationThe filtration
  6. concentrationwas concentrated
  7. customto dry
  8. washeluting with 0 to 40% EtOAc in Hexane

출처 및 근거

ORD 기록
ord-d6b50734fdab42abaef84eeb7dbd4c9d
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09440958B2

연결된 노트

불러오는 중…