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 268607노트

반응식

HRID 268607 반응식
[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]

참가 물질

5

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-6a8e00c363c7450bb99b112217215624
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07446115B2

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