Triethylamine → 3-Methyl-1-(5-nitro-pyridin-2-ylmethyl)azetidin-3-ol

HRID 55889노트

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HRID 55889 반응식
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:10]OS(C)(=O)=O)=[N:8][CH:9]=1)([O-:3])=[O:2].[CH3:16][C:17]1([OH:21])[CH2:20][NH:19][CH2:18]1.C(N(CC)CC)C>CO.CO.C1COCC1>[CH3:16][C:17]1([OH:21])[CH2:20][N:19]([CH2:10][C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][N:8]=2)[CH2:18]1

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 115427823-Methylazetidin-3-olHCID 86641144Methanesulfonic acid 5-nitro-pyridin-2-ylmethyl ester

생성물 1

HCID 903591743-Methyl-1-(5-nitro-pyridin-2-ylmethyl)azetidin-3-ol수율 71.3%

시약·촉매·용매 2

HCID 887Methanol용매HCID 21899815MeOH tetrahydrofuran용매

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온도
0 °C

실험 절차

To a solution of 52 (0.5 g, 2.2 mmol) in MeOH (25 mL) was added Ambersep-900 OH resin (50 g) filtered to separate the resin and concentrated to obtain the free base. The free base was dissolved in MeOH-THF (10 mL, 1:1) and cooled to 0° C. 3-methyl-azetidin-3-ol (0.53 g, 4.3 mmol) and triethylamine (0.7 mL, 4.3 mmol) were added and the reaction mixture warmed to rt and stirred for 16 h. The reaction mixture was concentrated and the crude compound was purified by silica gel column chromatography (100-200 mesh), eluting with 3% MeOH/CHCl3 to give the desired compound (0.35 g, 48%, over two steps) as a pale yellow liquid. Rf: 0.3 (10% MeOH/DCM); (m/z): 224 [MH]+; 1H NMR (400 MHz, DMSO-d6): δ 9.27 (1H, d, J=2.4 Hz), 8.56 (1H, dd, J=8.8, 2.8 Hz), 7.64 (1H, d, J=8.8 Hz), 5.22 (1H, s), 3.85 (2H, s), 3.36-3.26 (2H, m), 3.02-3.00 (2H, m), 1.38 (3H, s).

후처리

  1. filtrationfiltered
  2. customto separate the resin
  3. concentrationconcentrated
  4. customto obtain the free base
  5. temperaturethe reaction mixture warmed to rt
  6. concentrationThe reaction mixture was concentrated
  7. customthe crude compound was purified by silica gel column chromatography (100-200 mesh)
  8. washeluting with 3% MeOH/CHCl3

출처 및 근거

ORD 기록
ord-155fd89aab6849cea7b77783367c4e9c
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09433622B2

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