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

HRID 1026449ノート

反応式

HRID 1026449 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-cc27ca93c42345fcae0b66d1476260f8
出典データセット
uspto-grants-2014_05
特許番号
US08729072B2

反応ノート

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