Carbon Dioxide → N-[(S)-6-(1-hydroxy-1-methylethyl)-1,2,3,4-tetrahydronaphthalen-2-yl]-4-[(S)-1-(tetrahydrofuran-2-yl)methoxy]benzamide

HRID 1913823ノート

反応式

HRID 1913823 の反応式
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH2:8][C@@H:7]([NH:12][C:13](=[O:27])[C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:21][C@@H:22]3[CH2:26][CH2:25][CH2:24][O:23]3)=[CH:16][CH:15]=1)[CH2:6][CH2:5]2.C(=O)=[O:29].C[Li].[CH2:33]([Li])[CH2:34][CH2:35]C>O.CC(C)=O.C1COCC1>[OH:29][C:34]([C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH2:8][C@@H:7]([NH:12][C:13](=[O:27])[C:14]1[CH:15]=[CH:16][C:17]([O:20][CH2:21][C@@H:22]3[CH2:26][CH2:25][CH2:24][O:23]3)=[CH:18][CH:19]=1)[CH2:6][CH2:5]2)([CH3:35])[CH3:33]

参加物

8

反応物 4

HCID 280Carbon DioxideHCID 67545579N-((S)-6-Bromo-1,2,3,4-tetrahydronaphthalen-2-yl)-4-[(S)-1-(tetrahydrofuran-2-yl)methoxy]benzamideHCID 178418339ButyllithiumHCID 178418348HCID 178418348、化合物

生成物 1

HCID 67545052N-[(S)-6-(1-hydroxy-1-methylethyl)-1,2,3,4-tetrahydronaphthalen-2-yl]-4-[(S)-1-(tetrahydrofuran-2-yl)methoxy]benzamide

試薬・触媒・溶媒 3

HCID 180Acetone溶媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

A mixture of N-((S)-6-bromo-1,2,3,4-tetrahydronaphthalen-2-yl)-4-[(S)-1-(tetrahydrofuran-2-yl)methoxy]benzamide (1.0 g) and THF (10 ml) was cooled to −78° C. (dry ice bath), and a solution of methyllithium (2.0 ml; 1.6 M in diethyl ether) was added dropwise. One minute after the addition had ended, a solution of butyllithium (1.4 ml; 2.5 M in toluene) was added dropwise. One minute after the addition had ended, acetone (0.14 g) was added. After warming to room temperature, the reaction mixture was diluted with water and extracted with ethyl acetate. The organic phases were dried over magnesium sulfate and concentrated. The residue was chromatographed on silica gel (eluent: 1:2 heptane/ethyl acetate). The product was thus obtained with the molecular weight of 409.53 (C25H31NO4); MS (ESI): 410 (M+H+).

後処理

  1. additionOne minute after the addition
  2. additionOne minute after the addition
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic phases were dried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was chromatographed on silica gel (eluent: 1:2 heptane/ethyl acetate)
  7. customThe product was thus obtained with the molecular weight of 409.53 (C25H31NO4)

出典と根拠

ORDレコード
ord-d6722344340a4c2ab51968ac4126f02f
出典データセット
uspto-grants-2013_12
特許番号
US08609731B2

反応ノート

読み込み中…