Benzyl isocyanate → HCID 89615895, compound

HRID 1747750Notes

Reaction equation

HRID 1747750 reaction equation
[CH2:1]([N:8]=[C:9]=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:11]([C:15]1([CH2:25][CH:26]([CH3:28])[CH3:27])[C:19]2[CH2:20][NH:21][CH2:22][CH2:23][C:18]=2[C:17](=[O:24])[O:16]1)[CH:12]([CH3:14])[CH3:13]>ClCCl>[CH2:1]([NH:8][C:9]([N:21]1[CH2:22][CH2:23][C:18]2[C:17](=[O:24])[O:16][C:15]([CH2:25][CH:26]([CH3:28])[CH3:27])([CH2:11][CH:12]([CH3:14])[CH3:13])[C:19]=2[CH2:20]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 76639Benzyl isocyanateHCID 117901115HCID 117901115, compound

Product 1

HCID 89615895HCID 89615895, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Benzyl isocyanate (0.04 g, 0.3 mmol) was added to a solution of 3,3-diisobutyl-4,5,6,7-tetrahydrofuro[3,4-c]pyridin-1(3H)-one (0.075 g, 0.30 mmol prepared in a manner analogous to compound 2) in dichloromethane (10 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 (0.042 g, 36%). 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 0.75-0.93 (m, 12H), 1.39-1.60 (m, 4H), 1.77-1.92 (m, 2H), 2.28-2.45 (m, 2H), 3.36-3.55 (m, 2H), 4.03-4.18 (m, 2H), 4.34-4.48 (m, 2H), 4.85-5.03 (m, 1H), 7.17-7.39 (m, 5H).

Workup

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

Sources & evidence

ORD record
ord-29041d7973754771ac524bd79fe8c1c8
Source dataset
uspto-grants-2015_10
Patent number
US09150582B2

Reaction notes

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