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

HRID 494662Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 494662
[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]

Komponenten

6

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-10256d67979b4740b614881e69d717c1
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07538105B2

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