Triacetoxyperiodinane → Benzyl 4-formylpiperidine-1-carboxylate

HRID 220830

반응식

HRID 220830 반응식
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[CH2:23]([O:30][C:31]([N:33]1[CH2:38][CH2:37][CH:36]([CH2:39][OH:40])[CH2:35][CH2:34]1)=[O:32])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>ClCCl.C(Cl)(Cl)Cl.O>[CH2:23]([O:30][C:31]([N:33]1[CH2:38][CH2:37][CH:36]([CH:39]=[O:40])[CH2:35][CH2:34]1)=[O:32])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

참가 물질

6

반응물 2

HCID 159087TriacetoxyperiodinaneHCID 736490Benzyl 4-(hydroxymethyl)piperidine-1-carboxylate

생성물 1

HCID 2776272Benzyl 4-formylpiperidine-1-carboxylate수율 66%

시약·촉매·용매 3

HCID 962Water용매HCID 6212Chloroform용매HCID 6344Dichloromethane용매

실험 절차

Dess-Martin reagent (17 g, 39.6 mmol) was added portion-wise to a solution of 4-hydroxymethyl-piperidine-1-carboxylic acid benzyl ester from Example E33.1 (8.33 g, 33 mmol) in dichloromethane (100 ml) at room temperature. The mixture was stirred for 3 h under an inert atmosphere then diluted with chloroform and water and the layers were partitioned. The organic layer was washed with brine, dried and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (eluant; 40% EtOAc:60% hexane) to yield the title compound (5.5 g, 66%).

후처리

  1. customthe layers were partitioned
  2. washThe organic layer was washed with brine
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography on silica gel (eluant; 40% EtOAc:60% hexane)

출처 및 근거

ORD 기록
ord-ce0d9e545c534132b12a3dca31da0c12
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08202858B2

연결된 노트

불러오는 중…