Phenyl isocyanate → HCID 68578459, compound

HRID 639506Notes

Reaction equation

HRID 639506 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:6][C@H:7]3[N:18]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:17][CH2:16][C@@:13]4([C:14]=2[CH:15]=1)[C@H:8]3[CH2:9][CH2:10][CH2:11][CH2:12]4.C(N(CC)CC)C.[C:33]1([N:39]=[C:40]=[O:41])[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>ClCCl>[NH:39]([C:40]([O:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:6][C@H:7]3[N:18]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:17][CH2:16][C@@:13]4([C:14]=2[CH:15]=1)[C@H:8]3[CH2:9][CH2:10][CH2:11][CH2:12]4)=[O:41])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

5

Reactant 3

HCID 7672Phenyl isocyanateHCID 8471TriethylamineHCID 59254973HCID 59254973, compound

Product 1

HCID 68578459HCID 68578459, compoundYield 91.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 3-hydroxy-N-(tert-butyloxycarbonyl)morphinan (9 mg, 0.026 mmol) and triethylamine (10 μL, 0.04 mmol) in dry dichloromethane (0.3 mL) was added phenyl isocyanate (4 μL, 0.045 mmol) and the mixture was stirred for 1 h. After starting material disappeared on TLC, solvent was removed and column chromatography gave 11 mg (90%) of the title compound: 1H NMR (300 MHz, CDCl3) δ7.4 (2H, d); 7.3 (2H, t); 7.1 (3H, m); 6.9 (2H, m); 4.3 (1H, m); 3.8 (1H, m); 3.1 (1H, d. d.); 2.4˜2.8 (2H, m); 2.3 (1H, m); 1.3 (9H, s); 1.0˜1.7 (10H, m).

Workup

  1. customwas removed

Sources & evidence

ORD record
ord-56cc865a234640cfa74f80f40bbbef69
Source dataset
uspto-grants-2010_04
Patent number
US07691874B2

Reaction notes

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