1,2-Dichloroethane → tert-butyl 2,4-dioxo-5,6,7,7a-tetrahydro-4aH-cyclopenta[b]pyridine-1-carboxylate

HRID 885902

반응식

HRID 885902 반응식
[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:13][CH2:12][CH2:11][CH:10]1[C:14]([OH:16])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(Cl)CCl.[CH3:21][C:22]1(C)OC(=O)CC(=O)[O:23]1.OS([O-])(=O)=O.[Na+]>C(Cl)Cl.CN(C1C=CN=CC=1)C.CCOC(C)=O>[O:23]=[C:22]1[N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH:9]2[CH2:13][CH2:12][CH2:11][CH:10]2[C:14](=[O:16])[CH2:21]1

참가 물질

8

반응물 4

HCID 111,2-DichloroethaneHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 516919Sodium BisulfateHCID 35647322-((tert-Butoxycarbonyl)amino)cyclopentanecarboxylic acid

생성물 1

HCID 86642118tert-butyl 2,4-dioxo-5,6,7,7a-tetrahydro-4aH-cyclopenta[b]pyridine-1-carboxylate수율 93.1%

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

To a stirred solution of 2-[(tert-butoxycarbonyl)amino]cyclopentanecarboxylic acid (0.24 g, 1.06 mmol) in DCM (4.5 mL) was added EDC (0.31 g, 1.59 mmol), DMAP (0.19 g, 1.59 mmol) and Meldrum's acid (0.15 g, 1.06 mmol). After stirring for 18 h at r.t., the reaction mixture was poured into aqueous 1M NaHSO4 solution (5 mL) and extracted with DCM (3×20 mL). The combined organics were dried over MgSO4, filtered and concentrated in vacuo to give a clear yellow oil which was dissolved in EtOAc (5 mL) and heated to 80° C. for 18 h. The reaction mixture was then cooled and concentrated in vacuo to give the title compound (0.25 g, 42%) as a yellow solid that was used without further purification. δH (CDCl3) 4.64-4.55 (1H, m), 2.98-2.92 (1H, m), 2.37-2.20 (2H, m), 1.99-1.60 (6H, m), 1.58 (9H, s). LCMS (ES+) 198.0 ((M−tBu)+H)+.

후처리

  1. extractionextracted with DCM (3×20 mL)
  2. dry with materialThe combined organics were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto give a clear yellow oil which
  6. temperatureheated to 80° C. for 18 h
  7. temperatureThe reaction mixture was then cooled
  8. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-c5e322381b244f1188d9e42a010d8aaf
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08242116B2

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