Benzyl isocyanate → HCID 89615896, compound

HRID 1747744Notes

Reaction equation

HRID 1747744 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2([CH2:18][CH:19]([CH3:21])[CH3:20])[C:12]3[CH2:13][NH:14][CH2:15][CH2:16][C:11]=3[C:10](=[O:17])[O:9]2)[CH:5]=[CH:6][CH:7]=1.[CH2:22]([N:29]=[C:30]=[O:31])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>ClCCl>[CH2:22]([NH:29][C:30]([N:14]1[CH2:15][CH2:16][C:11]2[C:10](=[O:17])[O:9][C:8]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=3)([CH2:18][CH:19]([CH3:21])[CH3:20])[C:12]=2[CH2:13]1)=[O:31])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 76639Benzyl isocyanateHCID 117901152HCID 117901152, compound

Product 1

HCID 89615896HCID 89615896, compoundYield 104%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-(3-chlorophenyl)-3-isobutyl-4,5,6,7-tetrahydrofuro[3,4-c]pyridin-1(3H)-one (70 mg, 0.23 mmol) and benzyl isocyanate (42 μL, 0.34 mmol) in dichloromethane (5 mL) 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 (105 mg, 100%). 1H NMR (300 Hz, CDCl3) δ 0.85 (d, J=6.0, 3H), 0.93 (d, J=6.0, 3H), 1.55-1.70 (m, 1H), 1.72-1.82 (m, 1H), 2.20-2.40 (m, 3H), 3.15-3.29 (m, 1H), 3.49-3.61 (m, 1H), 3.89 (d, J=18.0, 1H), 4.39 (d, J=3.0, 2H), 4.48 (d, J=18.0, 1H), 5.22 (t, J=6.0, 1H), 7.14-7.38 (m, 9H).

Workup

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

Sources & evidence

ORD record
ord-7666ebff4a2941d38acb4ce0d54724ce
Source dataset
uspto-grants-2015_10
Patent number
US09150582B2

Reaction notes

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