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

HRID 1843206ノート

反応式

HRID 1843206 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-4dbe10da3d754baab46c1174f76007dc
出典データセット
uspto-grants-2015_02
特許番号
US08946213B2

反応ノート

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