Hydrochloric Acid → tert-butyl (2S)-2-[(1-cyclohexyl-3,4-dihydroisoquinolin-2(1H)-yl)carbonyl]pyrrolidine-1-carboxylate

HRID 2383016ノート

反応式

HRID 2383016 の反応式
CN1CCOCC1.[C:8]([O:12][C:13]([N:15]1[CH2:22][CH2:21][CH2:20][C@H:16]1[C:17]([OH:19])=O)=[O:14])([CH3:11])([CH3:10])[CH3:9].C(Cl)(=O)C(C)(C)C.Cl.[CH:31]1([CH:37]2[C:46]3[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=3)[CH2:40][CH2:39][NH:38]2)[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1.Cl>ClCCCl.CCOC(C)=O>[CH:31]1([CH:37]2[C:46]3[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=3)[CH2:40][CH2:39][N:38]2[C:17]([C@@H:16]2[CH2:20][CH2:21][CH2:22][N:15]2[C:13]([O:12][C:8]([CH3:9])([CH3:10])[CH3:11])=[O:14])=[O:19])[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36]1

参加物

8

反応物 5

HCID 313Hydrochloric AcidHCID 79724-Methylmorpholine2 回HCID 62493Pivaloyl chlorideHCID 850831,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)-HCID 675358401-Cyclohexyl-1,2,3,4-tetrahydroisoquinoline hydrochloride

生成物 1

HCID 68250501tert-butyl (2S)-2-[(1-cyclohexyl-3,4-dihydroisoquinolin-2(1H)-yl)carbonyl]pyrrolidine-1-carboxylate収率 109.2%

試薬・触媒・溶媒 2

HCID 111,2-Dichloroethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

N-methylmorpholine (0.873 mL) was added to a solution of 1-(tert-butoxycarbonyl)-L-proline (1.28 g) in 1,2-dichloroethane (10 mL) under ice-cooling, followed by further addition of pivaloyl chloride (0.734 mL). The reaction liquid was stirred for 1 hour, and N-methylmorpholine (1.09 mL) and 1-cyclohexyl-1,2,3,4-tetrahydroisoquinoline hydrochloride (1.00 g) were then added thereto. The mixture was stirred at room temperature for 15 hours. To the reaction solution were added EtOAc and an aqueous 1 M HCl solution. The organic layer was washed with water, a saturated aqueous sodium hydrogen carbonate solution, and saturated brine, dried over magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure to obtain tert-butyl (2S)-2-[(1-cyclohexyl-3,4-dihydroisoquinolin-2(1H)-yl)carbonyl]pyrrolidine-1-carboxylate (1.79 g).

後処理

  1. temperaturecooling
  2. customThe reaction liquid
  3. stirringThe mixture was stirred at room temperature for 15 hours
  4. washThe organic layer was washed with water
  5. dry with materiala saturated aqueous sodium hydrogen carbonate solution, and saturated brine, dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure

出典と根拠

ORDレコード
ord-69100ad6c9b9474bb07d7b99a9c83556
出典データセット
uspto-grants-2012_09
特許番号
US08263607B2

反応ノート

読み込み中…