Benzyl isocyanate → HCID 89615756, compound

HRID 1747749Notes

Reaction equation

HRID 1747749 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][C:28]([CH3:31])([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][C:28]([CH3:30])([CH3:29])[CH3:31])([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 117901255HCID 117901255, compound

Product 1

HCID 89615756HCID 89615756, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Benzyl isocyanate (0.02 g, 0.15 mmol) was added to a solution of 3-phenyl-3-neopentyl-4,5,6,7-tetrahydrofuro[3,4-c]pyridin-1(3H)-one (0.043 g, 0.15 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 (0.041 g, 63%). 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 0.87 (s, 9H), 1.88 (d, J=14.88 Hz, 1H), 2.28-2.43 (m, 2H), 2.38 (d, J=14.88 Hz, 1H), 3.16-3.28 (m, 1H), 3.53 (s, 1H), 3.96 (dt, J=19.03, 2.50 Hz, 1H), 4.42 (d, J=5.65 Hz, 2H), 4.59 (s, 1H), 4.88-4.99 (m, 1H), 7.20-7.41 (m, 10H).

Workup

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

Sources & evidence

ORD record
ord-6da84945851c4875bfdf820b133c84cd
Source dataset
uspto-grants-2015_10
Patent number
US09150582B2

Reaction notes

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