Triethylamine → 3-benzyloxycarbonyloxy-N-(benzyloxycarbonyl)morphinan

HRID 639505Notes

Reaction equation

HRID 639505 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:6][C@H:7]3[NH:18][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([CH2:24][CH3:25])CC)C.Cl[C:27]([O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:28]>ClCCl>[CH2:30]([O:29][C:27]([O:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:6][C@H:7]3[N:18]([C:27]([O:29][CH2:30][C:25]4[CH:24]=[CH:33][CH:32]=[CH:31][CH:36]=4)=[O:28])[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:28])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 5463854(-)-3-Hydroxymorphinan

Product 1

HCID 685768743-benzyloxycarbonyloxy-N-(benzyloxycarbonyl)morphinanYield 82.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 3-hydroxymorphinan (5 mg, 0.015 mmol) and triethylamine (13 μL, 0.091 mmol) in dry dichloromethane (0.3 mL) was added benzyl chloroformate (5.2 μL, 0.036 mmol) at 0° C. The reaction mixture was stirred for 2 h at room temperature. After starting material disappeared on TLC, solvent was removed and column chromatography gave 6.3 mg (80%) of title compound: 1H NMR (300 MHz, CDCl3) δ7.3˜7.6 (10H, m); 7.0 (2H, m); 6.9 (1H, m); 5.3 (2H, s); 5.1 (2H, s); 4.3 (1H, dd); 3.9 (1H, m); 3.1 (1H, m); 2.7 (2H, d); 2.3 (1H, m); 1.0˜1.8 (10H, m).

Workup

  1. customwas removed

Sources & evidence

ORD record
ord-a82bf1426e274ae4b1ab872a1b678083
Source dataset
uspto-grants-2010_04
Patent number
US07691874B2

Reaction notes

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