Benzyl isocyanate → HCID 89615848, compound

HRID 1747746Notes

Reaction equation

HRID 1747746 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][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[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][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)([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 117901417HCID 117901417, compound

Product 1

HCID 89615848HCID 89615848, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Benzyl isocyanate (0.02 6 g, 0.2 mmol) was added to a solution of 3-phenyl-3-benzyl-4,5,6,7-tetrahydrofuro[3,4-c]pyridin-1(3H)-one (0.05 g, 0.16 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 (0.036 g, 50%). 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 1.93-2.08 (m, 1H), 2.11-2.23 (m, 1H), 3.11-3.35 (m, 2H), 3.39-3.49 (m, 1H), 3.52-3.62 (m, 1H), 3.97-4.08 (m, 1H), 4.42 (dd, J=5.27, 2.64 Hz, 2H), 4.59 (dt, J=19.12, 2.12 Hz, 1H), 4.90 (t, J=5.46 Hz, 1H), 7.15-7.47 (m, 15H).

Workup

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

Sources & evidence

ORD record
ord-a35aa4696be54b5f8c12fe0ae420857e
Source dataset
uspto-grants-2015_10
Patent number
US09150582B2

Reaction notes

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