Triethylamine → HCID 131733515, compound

HRID 2281219Notes

Reaction equation

HRID 2281219 reaction equation
[OH:1][C:2]1([C:10]#[N:11])[CH:7]2[CH2:8][CH2:9][N:4]([CH2:5][CH2:6]2)[CH2:3]1.C(N(CC)CC)C.[N:19]([C:22]([C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([C:31]([CH3:33])=[CH2:32])[CH:26]=1)([CH3:24])[CH3:23])=[C:20]=[O:21]>C(#N)C.O1CCOCC1>[CH2:32]=[C:31]([C:27]1[CH:26]=[C:25]([C:22]([NH:19][C:20](=[O:21])[O:1][C:2]2([C:10]#[N:11])[CH:7]3[CH2:8][CH2:9][N:4]([CH2:5][CH2:6]3)[CH2:3]2)([CH3:24])[CH3:23])[CH:30]=[CH:29][CH:28]=1)[CH3:33]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2972833-Hydroxyquinuclidine-3-carbonitrileHCID 6041521-(1-Isocyanato-1-methylethyl)-3-(1-methylethenyl)benzene

Product 1

HCID 131733515HCID 131733515, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 22504236Acetonitrile dioxaneSolvent

Procedure

To a solution of 3-hydroxyquinuclidine-3-carbonitrile (38 mg, 0.25 mmol) in acetonitrile/dioxane (3 mL) at room temperature was added triethylamine (7.0 uL, 0.05 mmol). The reaction mixture was stirred for 15 min and 1-(2-isocyanatopropan-2-yl)-3-(prop-1-en-2-yl)benzene (49.0 uL, 0.248 mmol) was added dropwise. The reaction was stirred for a period of 18 h at 65° C. and concentrated. The crude material was purified on a combiflash (SiO2 cartridge, CHCl3 and 2N NH3 in MeOH) to afford the corresponding carbamate as a clear oil (57 mg, 65%). 1H NMR (400 MHz, CDCl3) δ 7.42-7.20 (s, 5H), 6.61 (s, 1H), 5.11 (s, 1H), 3.29 (d, J=12.0 Hz, 1H), 3.09 (d, J=12.0 Hz, 1H), 2.93 (d, J=4.0 Hz, 2H), 2.79-2.68 (m, 2H), 2.13 (s, 6H) 2.05-2.00 (m, 2H), 1.91 (s, 3H), 1.87 (s, 2H), 1.50-1.37 (m, 2H) ppm. 13C NMR (100 MHz, CDCl3) δ 135.4, 128.7, 125.2, 124.5, 124.0, 122.0, 112.9, 61.2, 47.0, 46.2, 32.4, 31.8, 29.9, 29.4, 29.2, 26.6, 25.7, 23.7, 22.8, 22.2, 19.2 ppm. Purity: >99% UPLCMS (210 nm); retention time 0.81 min; (M+1) 354.

Workup

  1. stirringThe reaction was stirred for a period of 18 h at 65° C.
  2. concentrationconcentrated
  3. customThe crude material was purified on a combiflash (SiO2 cartridge, CHCl3 and 2N NH3 in MeOH)

Sources & evidence

ORD record
ord-3f496e2f94664e19b5151d3b620abb93
Source dataset
uspto-grants-2015_09
Patent number
US09139580B2

Reaction notes

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