tert-Butyl methyl ether → Cis-2-(4-Fluoro-Phenyl)-Cyclopropyl-Carbamic Acid Tert-Butyl Ester

HRID 1479150노트

반응식

HRID 1479150 반응식
[Na].S(N[N:13]=[CH:14][C:15]1C=CC=C[C:16]=1[C:21]1[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=1)(C1C=CC(C)=CC=1)(=O)=O.[C:28]([O:32][C:33](=[O:37])NC=C)([CH3:31])([CH3:30])[CH3:29].O1CCOCC1.C(OC)(C)(C)C>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.O>[C:28]([O:32][C:33](=[O:37])[NH:13][C@@H:14]1[CH2:15][C@@H:16]1[C:21]1[CH:22]=[CH:23][C:24]([F:27])=[CH:25][CH:26]=1)([CH3:31])([CH3:30])[CH3:29]

참가 물질

7

반응물 4

HCID 15413tert-Butyl methyl etherHCID 312751,4-Dioxane2회HCID 251740tert-butyl N-ethenylcarbamateHCID 1317365734-Fluorophenyl benzaldehyde-tosylhydrazone sodium salt

생성물 1

HCID 89760766Cis-2-(4-Fluoro-Phenyl)-Cyclopropyl-Carbamic Acid Tert-Butyl Ester수율 215.4%

시약·촉매·용매 2

HCID 66133Benzyl triethylammonium chloride촉매HCID 962Water용매

실험 절차

4-Fluorophenyl benzaldehyde-tosylhydrazone sodium salt (786 mg, 2.5 mmol), N-vinyl-carbamic acid tert-butyl ester (1.432 g, 10 mmol) and benzyltriethylammonium chloride (57 mg, 0.25 mmol) were covered with dioxane (11 ml) under argon. Rh2(OAc)4 (11 mg, 0.025 mmol) was added and the suspension stirred at room temperature for 15 minutes. The slurry became thick and difficult to stir so a further 4 ml of dioxane was added. The mixture was stirred at 75° C. for 2 hours, then shaken between tBuOMe and water. The organic phase was washed with water and NaCl (satd), dried over MgSO4 and evaporated to yield a brown viscous oil (1.353 g), which was chromatographed on silica to yield 2-(4-fluoro-phenyl)-cyclopropyl-carbamic acid tert-butyl ester 369 mg (59%, m.p. 117-118° C.) cis and 125 mg (20% m.p. 102-105° C.) trans.

후처리

  1. additionwas added
  2. stirringThe mixture was stirred at 75° C. for 2 hours
  3. washThe organic phase was washed with water and NaCl (satd)
  4. dry with materialdried over MgSO4
  5. customevaporated

출처 및 근거

ORD 기록
ord-56b31186a9f74f389e497816396a1ee4
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09408392B2

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