Potassium Carbonate → tert-butyl (2R,5S)-5-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-[(E)-2-(2-nitrophenyl)ethenyl]morpholine-4-carboxylate

HRID 629696

반응식

HRID 629696 반응식
[Si:1]([O:8][CH2:9][C@H:10]1[N:15]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:14][C@@H:13]([CH:23]=O)[O:12][CH2:11]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Br-].[N+:26]([C:29]1[CH:54]=[CH:53][CH:52]=[CH:51][C:30]=1[CH2:31][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O-:28])=[O:27].C(=O)([O-])[O-].[K+].[K+]>COCCOC>[Si:1]([O:8][CH2:9][C@H:10]1[N:15]([C:16]([O:18][C:19]([CH3:21])([CH3:22])[CH3:20])=[O:17])[CH2:14][C@@H:13](/[CH:23]=[CH:31]/[C:30]2[CH:51]=[CH:52][CH:53]=[CH:54][C:29]=2[N+:26]([O-:28])=[O:27])[O:12][CH2:11]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 10885283(2-Nitrobenzyl)triphenylphosphonium bromideHCID 86726303Tert-butyl (2S,5S)-5-(((tert-butyldimethylsilyl)oxy)methyl)-2-formylmorpholine-4-carboxylate

생성물 1

HCID 86726304tert-butyl (2R,5S)-5-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-[(E)-2-(2-nitrophenyl)ethenyl]morpholine-4-carboxylate

시약·촉매·용매 1

HCID 80711,2-Dimethoxyethane용매

실험 절차

To tert-butyl (2S,5S)-5-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-formylmorpholine-4-carboxylate (1 eq.) in DME (0.2 M) at rt were added (2-nitrobenzyl)(triphenyl)phosphonium bromide (1.1 eq.), potassium carbonate (2 eq.) and 18-C-6 (0.1 eq.). The reaction mixture was stirred at rt for 12 hrs, filtered on celite and the filtrate was concentrated under reduced pressure. The crude product was purified by automated SiO2 flash chromatography system using solvent gradient of 10% to 60% EtOAc/Hex to afford the desired compound

후처리

  1. filtrationfiltered on celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe crude product was purified by automated SiO2 flash chromatography system

출처 및 근거

ORD 기록
ord-f29b052624a44ae8a3f46fdc28e7f0ea
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09315475B2

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