Benzylacetylene → Propyl [7-(5-benzyl-1H-1,2,3-triazol-1-yl)-4-fluoro-6,7,8,9-tetrahydropyrido[1,2-a]indol-10-yl]acetate

HRID 1944023ノート

反応式

HRID 1944023 の反応式
[N:1]([CH:4]1[CH2:24][N:8]2[C:9]3[C:14]([C:15]([CH2:16][C:17]([O:19][CH2:20][CH2:21][CH3:22])=[O:18])=[C:7]2[CH2:6][CH2:5]1)=[CH:13][CH:12]=[CH:11][C:10]=3[F:23])=[N+:2]=[N-:3].[CH2:25]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:26]#[CH:27]>C1C=CC=CC=1.CC1C([Ru+])(C)C(C)=C(C)C=1C.ClC1CCC=CCCC=1>[CH2:25]([C:26]1[N:1]([CH:4]2[CH2:24][N:8]3[C:9]4[C:14]([C:15]([CH2:16][C:17]([O:19][CH2:20][CH2:21][CH3:22])=[O:18])=[C:7]3[CH2:6][CH2:5]2)=[CH:13][CH:12]=[CH:11][C:10]=4[F:23])[N:2]=[N:3][CH:27]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

参加物

5

反応物 2

HCID 575753BenzylacetyleneHCID 86645392Propyl (7-azido-4-fluoro-6,7,8,9-tetrahydropyrido[1,2-a]indol-10-yl)acetate

生成物 1

HCID 86645394Propyl [7-(5-benzyl-1H-1,2,3-triazol-1-yl)-4-fluoro-6,7,8,9-tetrahydropyrido[1,2-a]indol-10-yl]acetate

試薬・触媒・溶媒 2

HCID 178425933HCID 178425933、化合物触媒HCID 241Benzene溶媒

実験手順

To a stirred solution of propyl (7-azido-4-fluoro-6,7,8,9-tetrahydropyrido[1,2-a]indol-10-yl)acetate (1 eq) and prop-2-yn-1-ylbenzene (1.5 eq) in benzene (0.3M) at room temperature was added chloro(1,5-cyclooctadiene) (pentamethylcyclopentadienyl)-ruthenium(II) (0.1 eq). The reaction mixture was flushed with nitrogen then aged at 80° C. for overnight, cooled to room temperature, filtered through silica gel, washed with EtOAc and concentrated. The residue was purified by column chromatography on silica gel eluting with EtOAc/Hexane (0 to 50%) to give the desired material as a brown oil. The racemic mixture was resolved by HPLC using a 50×400 mm Chiralpak AD column eluting with 15% MeOH, 15% EtOH, 69.75% Hexanes and 0.25% Et3N at 50 mL/min and 254 nm to afford the desired chiral ester with retention time of 9.6 and 11.6 min respectively.

後処理

  1. customThe reaction mixture was flushed with nitrogen
  2. filtrationfiltered through silica gel
  3. washwashed with EtOAc
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography on silica gel eluting with EtOAc/Hexane (0 to 50%)

出典と根拠

ORDレコード
ord-9209c555e0de44ec8bcebb0e34109b7f
出典データセット
uspto-grants-2013_03
特許番号
US08394819B2

反応ノート

読み込み中…