Benzyl isocyanate → HCID 89615931, compound

HRID 1747742Notes

Reaction equation

HRID 1747742 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:15]2([CH3:25])[C:19]3[CH2:20][NH:21][CH2:22][CH2:23][C:18]=3[C:17](=[O:24])[O:16]2)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:26]([N:33]=[C:34]=[O:35])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>ClCCl>[CH2:26]([NH:33][C:34]([N:21]1[CH2:22][CH2:23][C:18]2[C:17](=[O:24])[O:16][C:15]([C:11]3[CH:12]=[CH:13][CH:14]=[C:9]([O:8][CH2:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)[CH:10]=3)([CH3:25])[C:19]=2[CH2:20]1)=[O:35])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

4

Reactant 2

HCID 76639Benzyl isocyanateHCID 117901099HCID 117901099, compound

Product 1

HCID 89615931HCID 89615931, compoundYield 61.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-(3-benzyloxyphenyl)-3-methyl-4,5,6,7-tetrahydrofuro[3,4-c]pyridin-1(3H)-one (50 mg, 0.15 mmol) and benzyl isocyanate (27 μL, 0.22 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 (43 mg, 61.6%). 1H NMR (300 Hz, CDCl3) δ 1.84 (s, 3H), 2.38 (br s, 2H), 3.26-3.32 (m, 1H), 3.51-3.58 (m, 1H), 3.79 (d, J=18.0, 1H), 4.37-4.30 (m, 3H), 4.94 (t, J=6.0, 1H), 5.04 (s, 2H), 6.87-6.94 (m, 3H), 7.24-7.39 (m, 11H).

Workup

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

Sources & evidence

ORD record
ord-070621c65179464f9127bce0c8b0e841
Source dataset
uspto-grants-2015_10
Patent number
US09150582B2

Reaction notes

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