Triethylamine → HCID 67979956, 화합물

HRID 1622304노트

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HRID 1622304 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([CH3:17])([C:14]([OH:16])=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.CN(C(F)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.[CH2:41]1[C:50]2[C:45](=[CH:46][C:47]([C:51]([O:53][CH3:54])=[O:52])=[CH:48][CH:49]=2)[CH2:44][CH2:43][NH:42]1>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][C:11]([C:14]([N:42]2[CH2:43][CH2:44][C:45]3[C:50](=[CH:49][CH:48]=[C:47]([C:51]([O:53][CH3:54])=[O:52])[CH:46]=3)[CH2:41]2)=[O:16])([CH3:17])[CH2:12][CH2:13]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

참가 물질

6

반응물 4

HCID 8471Triethylamine2회HCID 2774761Tetramethylfluoroformamidinium hexafluorophosphateHCID 232828481-[(Tert-butoxy)carbonyl]-4-methylpiperidine-4-carboxylic acidHCID 42614607Methyl 1,2,3,4-tetrahydroisoquinoline-6-carboxylate hydrochloride

생성물 1

HCID 67979956HCID 67979956, 화합물수율 82%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A solution of 1-(tert-butoxycarbonyl)-4-methylpiperidine-4-carboxylic acid (0.830 g, 3.41 mmol) and triethylamine (0.792 mL, 5.68 mmol) in DMF (11.0 mL) was treated with TFFH (1.13 g, 4.26 mmol). The resulting mixture was stirred at rt for 30 min and then methyl 1,2,3,4-tetrahydroisoquinoline-6-carboxylate hydrochloride (0.647 g, 2.84 mmol) and triethylamine (0.792 mL, 5.68 mmol) were added. The reaction mixture was stirred at rt for 2 days and then extracted with EtOAc three times. The combined organic phases were washed with water and brine, dried over Na2SO4, filtered and concentrated. Purification of the resulting residue by column chromatography (SiO2, 0-100% EtOAc in hexane) provided methyl 2-{[1-(tert-butoxycarbonyl)-4-methylpiperidin-4-yl]carbonyl}-1,2,3,4-tetrahydroisoquinoline-6-carboxylate (0.959 g, 82%). LC-MS: (FA) ES+ 439 (M+Na); 1H NMR (400 MHz, CDCl3) δ 7.85 (dd, J=10.1, 2.2 Hz, 2H), 7.19 (d, J=8.0 Hz, 1H), 4.79 (s, 2H), 3.95-3.77 (m, 5H), 3.67 (d, J=38.1 Hz, 2H), 3.21 (s, 2H), 2.92 (t, J=5.7 Hz, 2H), 2.24-2.10 (m, 2H), 1.61 (d, J=10.8 Hz, 1H), 1.44 (d, J=5.0 Hz, 10H), 1.33 (d, J=3.6 Hz, 3H).

후처리

  1. stirringThe reaction mixture was stirred at rt for 2 days
  2. extractionextracted with EtOAc three times
  3. washThe combined organic phases were washed with water and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification of the resulting residue by column chromatography (SiO2, 0-100% EtOAc in hexane)

출처 및 근거

ORD 기록
ord-efe5648b45ae4e7e82d391a52217d12f
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08778931B2

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