Ammonium Acetate → Ethyl (5R)-2-amino-5-methyl-1-cyclopentene-1-carboxylate

HRID 80995노트

반응식

HRID 80995 반응식
C([O-])(=O)C.[NH4+:5].[CH3:6][CH:7]1[CH2:11][CH2:10][C:9](=O)[C@@H:8]1[C:13]([O:15][CH2:16][CH3:17])=[O:14]>CO>[NH2:5][C:9]1[CH2:10][CH2:11][C@@H:7]([CH3:6])[C:8]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14]

참가 물질

4

반응물 2

HCID 517165Ammonium AcetateHCID 86618740(R)-ethyl 2-methyl-5-oxocyclopentanecarboxylate

생성물 1

HCID 59671147Ethyl (5R)-2-amino-5-methyl-1-cyclopentene-1-carboxylate수율 97%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

Ammonium acetate (240.03 g, 3113.9 mmol) was added to a solution of (R)-ethyl 2-methyl-5-oxocyclopentanecarboxylate (106.0 g, 622.78 mmol) in MeOH (1.2 L). The reaction mixture was stirred at room temperature under nitrogen for 20 hours, after which it was complete as judged by TLC and HPLC. The reaction mixture was concentrated to remove MeOH. The resulting residue was dissolved in DCM, washed twice with H2O, once with brine, dried (Na2SO4), filtered, and concentrated to give (R)-ethyl 2-amino-5-methylcyclopent-1-enecarboxylate (102 g, 97% yield) as an oil. LC/MS (APCI+) m/z 170 [M+H]+.

후처리

  1. concentrationThe reaction mixture was concentrated
  2. customto remove MeOH
  3. dissolutionThe resulting residue was dissolved in DCM
  4. washwashed twice with H2O, once with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-8424087ad2964ac8b9f9c92003b78a61
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846683B2

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