Benzyl isocyanate → HCID 89615887, compound

HRID 1747748Notes

Reaction equation

HRID 1747748 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][OH:28])[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][OH:28])([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 117901411HCID 117901411, compound

Product 1

HCID 89615887HCID 89615887, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Benzyl isocyanate (0.069 g, 0.52 mmol) was added to a solution of 3-phenyl-3-hydroxymethyl-4,5,6,7-tetrahydrofuro[3,4-c]pyridin-1(3H)-one (0.128 g, 0.52 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 (0.101 g, 51%). 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 2.18-2.47 (m, 2H), 3.19-3.31 (m, 1H), 3.63 (dt, J=13.75, 4.99 Hz, 1H), 3.94-4.07 (m, 3H), 4.07-4.18 (m, 1H), 4.35 (d, J=5.65 Hz, 2H), 4.47 (d, J=18.84 Hz, 1H), 5.50 (t, J=5.65 Hz, 1H), 7.15-7.25 (m, 4H), 7.27-7.42 (m, 6H).

Workup

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

Sources & evidence

ORD record
ord-8c1bc4ef933e42cb994aeddc5e78489c
Source dataset
uspto-grants-2015_10
Patent number
US09150582B2

Reaction notes

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