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

HRID 2224982Notes

Reaction equation

HRID 2224982 reaction equation
[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]

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

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, 7 H), 0.91 (m, 8 H), 1.37 (m, 1 H), 1.60 (m, 1 H), 1.93 (m, 1 H), 3.49 (d, J=3.68 Hz, 2 H), 3.58 (s, 3 H), 4.21 (d, J=10.30 Hz, 1 H), 4.45 (d, J=10.30 Hz, 1 H), 5.00 (t, J=3.68 Hz, 1 H), 7.17 (m, 3 H), 7.30 (m, 1 H).

Workup

  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

Sources & evidence

ORD record
ord-179fbb0fad584c26846d2a6c46d271f4
Source dataset
uspto-grants-2008_05
Patent number
US07378414B2

Reaction notes

Loading…