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

HRID 494662Notes

Reaction equation

HRID 494662 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, 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).

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-10256d67979b4740b614881e69d717c1
Source dataset
uspto-grants-2009_05
Patent number
US07538105B2

Reaction notes

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