Benzyl isocyanate → HCID 89615827, compound

HRID 1747747Notes

Reaction equation

HRID 1747747 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][CH:28]([CH3:30])[CH3:29])[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][CH:28]([CH3:29])[CH3:30])([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 896147743-isobutyl-3-phenyl-4,5,6,7-tetrahydrofuro[3,4-c]pyridin-1(3H)-one

Product 1

HCID 89615827HCID 89615827, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Benzyl isocyanate (0.02 9 g, 0.22 mmol) was added to a solution of 3-phenyl-3-isobutyl-4,5,6,7-tetrahydrofuro[3,4-c]pyridin-1(3H)-one (0.05 g, 0.184 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 (0.051 g, 68%). 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 0.85 (d, J=6.40 Hz, 3H), 0.89-0.98 (m, 3H), 1.65 (ddd, J=13.56, 6.78, 4.90 Hz, 1H), 1.73-1.87 (m, 1H), 2.24-2.40 (m, 3H), 3.27 (ddd, J=13.56, 7.35, 5.09 Hz, 1H), 3.54 (dt, J=13.66, 5.23 Hz, 1H), 3.92 (dt, J=18.84, 2.64 Hz, 1H), 4.40 (d, J=5.65 Hz, 2H), 4.49 (dt, J=19.12, 2.12 Hz, 1H), 5.00 (t, J=5.46 Hz, 1H), 7.21-7.42 (m, 10H).

Workup

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

Sources & evidence

ORD record
ord-2f5f2330e9ee46e3bb14a5eba1bbc2ef
Source dataset
uspto-grants-2015_10
Patent number
US09150582B2

Reaction notes

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