1,2-Ethanediamine, N1,N1-dimethyl-N2-(phenylmethyl)- → 3-[Benzyl-(2-dimethylamino-ethyl)-carbamoyl]-3,4-dihydro-1h-isoquinoline-2-carboxylic acid tert-butyl ester

HRID 268607ノート

反応式

HRID 268607 の反応式
[CH3:1][C:2]([O:5][C:6]([N:8]1[C@H:17]([C:18]([OH:20])=O)[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])[CH3:3].CN(C(F)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH2:36]([NH:43][CH2:44][CH2:45][N:46]([CH3:48])[CH3:47])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>ClCCl>[C:2]([O:5][C:6]([N:8]1[CH:17]([C:18](=[O:20])[N:43]([CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH2:44][CH2:45][N:46]([CH3:48])[CH3:47])[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:1]

参加物

5

反応物 3

HCID 660291,2-Ethanediamine, N1,N1-dimethyl-N2-(phenylmethyl)-HCID 664088(3S)-2-((tert-butoxy)carbonyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acidHCID 2774761Tetramethylfluoroformamidinium hexafluorophosphate

生成物 1

HCID 210623603-[Benzyl-(2-dimethylamino-ethyl)-carbamoyl]-3,4-dihydro-1h-isoquinoline-2-carboxylic acid tert-butyl ester収率 26%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

To a solution of N-Boc-L-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (2.0 g, 7.2 mmole) in dichloromethane (20 mL) was added TFFH (1.91 g, 7.2 mmole). The mixture was cooled to 0° C. and N′-benzyl-N,N-dimethylethylenediamine (2.57 g, 14.4 mmole) was added to the reaction. The reaction was allowed to warm to room temperature and stirred for 6 h. The reaction was then quenched with water (20 mL), and the organic layer was dried over anhydrous sodium sulfate, filtered and concentrated. The organic residue was purified by flash chromatography on silica gel, eluting with dichloromethane/2.0 M ammonia in ethyl alcohol (96:4) to give 1d (0.81 g, 26%) as a pale yellow oil.

後処理

  1. temperatureto warm to room temperature
  2. customThe reaction was then quenched with water (20 mL)
  3. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe organic residue was purified by flash chromatography on silica gel
  7. washeluting with dichloromethane/2.0 M ammonia in ethyl alcohol (96:4)

出典と根拠

ORDレコード
ord-6a8e00c363c7450bb99b112217215624
出典データセット
uspto-grants-2008_11
特許番号
US07446115B2

反応ノート

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