Dimethyl Carbonate → Methyl 1-benzyl-2-oxoazepane-3-carboxylate

HRID 467470노트

반응식

HRID 467470 반응식
[CH2:1]([N:8]1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][C:9]1=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li+].CC([N-]C(C)C)C.[C:24](=O)([O:27]C)[O:25][CH3:26]>CCOCC>[CH2:1]([N:8]1[CH2:14][CH2:13][CH2:12][CH2:11][CH:10]([C:24]([O:25][CH3:26])=[O:27])[C:9]1=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 12021Dimethyl CarbonateHCID 14910681-Benzylazepan-2-oneHCID 2724682Lithium diisopropylamide

생성물 1

HCID 21902024Methyl 1-benzyl-2-oxoazepane-3-carboxylate

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

A cooled (−78° C.) solution of 1-2 (2 g, 9.84 mmol) in Et2O (50 ml) was treated with LDA (9.84 ml, 19.68 mmol) and stirred for 1 h. The mixture was treated with dimethyl carbonate (1.658 ml, 19.68 mmol), warmed to RT and stirred overnight. The mixture was quenched with 1N HCl and extracted twice with EtOAc. The organic phase was dried over Na2SO4, filtered and concentrated. The crude material was purified by gradient elution on silica gel (0 to 60% EtOAc in Hex) to yield a 1:1 mixture of 1-3 and starting material as a tan oil. Data for 1-3: LRMS m/z (M+H): 262.1.

후처리

  1. stirringstirred overnight
  2. customThe mixture was quenched with 1N HCl
  3. extractionextracted twice with EtOAc
  4. dry with materialThe organic phase was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude material was purified by gradient elution on silica gel (0 to 60% EtOAc in Hex)
  8. customto yield
  9. additiona 1:1 mixture of 1-3

출처 및 근거

ORD 기록
ord-41e3d9850e4744a88b246d49586fed64
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08623863B2

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