Acetic Acid → 7,7-Difluoro-3,4,6,7,8,9-hexahydropyrazino[1,2-a]indol-1(2H)-one

HRID 1026449노트

반응식

HRID 1026449 반응식
[NH2:1][CH2:2][CH2:3][N:4]1[C:12]2[CH2:11][C:10]([F:14])([F:13])[CH2:9][CH2:8][C:7]=2[CH:6]=[C:5]1[C:15]([O:17]CC)=O.C(O)(=O)C>C1(C)C=CC=CC=1>[F:13][C:10]1([F:14])[CH2:11][C:12]2[N:4]3[CH2:3][CH2:2][NH:1][C:15](=[O:17])[C:5]3=[CH:6][C:7]=2[CH2:8][CH2:9]1

참가 물질

4

반응물 2

HCID 176Acetic AcidHCID 86683733Ethyl 1-(2-Aminoethyl)-6,6-difluoro-4,5,6,7-tetrahydro-1H-indole-2-carboxylate

생성물 1

HCID 866837357,7-Difluoro-3,4,6,7,8,9-hexahydropyrazino[1,2-a]indol-1(2H)-one수율 53.3%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

Into a 250-mL round-bottom flask was placed a solution of 113n (10 g, 36.73 mmol, 1.00 equiv) in toluene (100 mL) and acetic acid (1.1 g, 18.32 mmol, 0.50 equiv). See FIG. 14. The resulting solution was heated to reflux for 2 h, cooled and concentrated under vacuum. The residue was triturated in 100 mL of dry ether. The crude product was purified by recrystallization from ethanol to afford 4.43 g (53%) of 113o as a white solid. MS-ESI: [M+H]+ 227. 1H NMR (300 MHz, DMSO) δ 2.10-2.24 (2H, m), 2.59-2.64 (2H, m), 3.17-3.27 (2H, m), 3.43-3.48 (2H, m), 3.88-3.92 (2H, m), 6.44 (1H, s), 7.56 (1H, s).

후처리

  1. customInto a 250-mL round-bottom flask was placed
  2. temperatureThe resulting solution was heated
  3. temperatureto reflux for 2 h
  4. temperaturecooled
  5. concentrationconcentrated under vacuum
  6. customThe residue was triturated in 100 mL of dry ether
  7. customThe crude product was purified by recrystallization from ethanol

출처 및 근거

ORD 기록
ord-cc27ca93c42345fcae0b66d1476260f8
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08729072B2

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