Triethylamine → [2-Methoxy-1-(3-methylbutyl)-1,4-dihydronaphthalen-1-yl]methyl isopropylcarbamate

HRID 494662ノート

反応式

HRID 494662 の反応式
[CH3:1][O:2][C:3]1[C:4]([CH2:18][OH:19])([CH2:13][CH2:14][CH:15]([CH3:17])[CH3:16])[C:5]2[C:10]([CH2:11][CH:12]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.C(N(CC)CC)C.[CH:27]([N:30]=[C:31]=[O:32])([CH3:29])[CH3:28]>ClCCl.CN(C)C1C=CN=CC=1>[CH:27]([NH:30][C:31](=[O:32])[O:19][CH2:18][C:4]1([CH2:13][CH2:14][CH:15]([CH3:16])[CH3:17])[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH2:11][CH:12]=[C:3]1[O:2][CH3:1])([CH3:29])[CH3:28]

参加物

6

反応物 3

HCID 8471TriethylamineHCID 61277Isopropyl isocyanate2 回HCID 68871071[2-Methoxy-1-(3-methylbutyl)-1,4-dihydronaphthalen-1-yl]methanol

生成物 1

HCID 68871317[2-Methoxy-1-(3-methylbutyl)-1,4-dihydronaphthalen-1-yl]methyl isopropylcarbamate収率 59%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of Example 179A (50 mg, 0.2 mmol) in dichloromethane (1 mL) was added triethylamine (0.13 mL, 1 mmol), 4-dimethylaminopyridine (9 mg, 0.08 mmol), and isopropyl isocyanate (0.1 mL, 1 mmol). The solution was stirred at room temperature for 18 h. After which, additional 5.0 equivalents (0.1 mL) of isopropyl isocyanate were added, and the solution was stirred for another 18 h. The solution was diluted with dichloromethane (2 mL), washed with water (2× 1 mL), dried (Na2SO4), and concentrated in vacuo. Column chromatography on silica (0-5% ethyl acetate/hexane) afforded product (39 mg, 59%). 1H NMR (300 MHz, CDCl3) δ ppm 0.70 (m, 7H), 0.91 (m, 8H), 1.37 (m, 1H), 1.60 (m, 1H), 1.93 (m, 1H), 3.49 (d, J=3.68 Hz, 2H), 3.58 (s, 3H), 4.21 (d, J=10.30 Hz, 1H), 4.45 (d, J=10.30 Hz, 1H), 5.00 (t, J=3.68 Hz, 1H), 7.17 (m, 3H), 7.30 (m, 1H).

後処理

  1. stirringthe solution was stirred for another 18 h
  2. washwashed with water (2× 1 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-10256d67979b4740b614881e69d717c1
出典データセット
uspto-grants-2009_05
特許番号
US07538105B2

反応ノート

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