Benzyl isocyanate → HCID 89615921, compound

HRID 1747745Notes

Reaction equation

HRID 1747745 reaction equation
[CH2:1]([N:8]=[C:9]=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:11]1([C:17]2([CH2:27][CH2:28][CH2:29][CH3:30])[C:21]3[CH2:22][NH:23][CH2:24][CH2:25][C:20]=3[C:19](=[O:26])[O:18]2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>ClCCl>[CH2:1]([NH:8][C:9]([N:23]1[CH2:24][CH2:25][C:20]2[C:19](=[O:26])[O:18][C:17]([CH2:27][CH2:28][CH2:29][CH3:30])([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:21]=2[CH2:22]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 76639Benzyl isocyanateHCID 117901171HCID 117901171, compound

Product 1

HCID 89615921HCID 89615921, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Benzyl isocyanate (0.02 g, 0.14 mmol) was added to a solution of 3-phenyl-3-butyl-4,5,6,7-tetrahydrofuro[3,4-c]pyridin-1(3H)-one (0.025 g, 0.09 mmol prepared in a manner analogous to compound 2) in dichloromethane (5 mL) and was stirred at room temperature for 1 h. The solvent was removed and the resulting residue was purified on silica to give the desired product (0.018 g, 50%). 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 0.79 (t, J=7.16 Hz, 3H), 1.06-1.33 (m, 4H), 1.83-1.97 (m, 1H), 2.14-2.43 (m, 3H), 3.18-3.31 (m, 1H), 3.36-3.51 (m, 1H), 3.85 (dt, J=18.84, 2.64 Hz, 1H), 4.26-4.39 (m, 3H), 4.90 (t, J=5.27 Hz, 1H), 7.11-7.36 (m, 10H).

Workup

  1. customThe solvent was removed
  2. customthe resulting residue was purified on silica

Sources & evidence

ORD record
ord-3673c1251d6d4f24918636542411866e
Source dataset
uspto-grants-2015_10
Patent number
US09150582B2

Reaction notes

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