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

HRID 55889ノート

反応式

HRID 55889 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 21899815MeOH tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-155fd89aab6849cea7b77783367c4e9c
出典データセット
uspto-grants-2016_09
特許番号
US09433622B2

反応ノート

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