1-Bromo-3-chloropropane → 3-(3-Chloropropyloxy)-N-(benzyloxycarbonyl)morphinan

HRID 639517Notes

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][CH2:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[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(=O)([O-])[O-].[K+].[K+].Br[CH2:36][CH2:37][CH2:38][Cl:39]>CN(C=O)C>[Cl:39][CH2:38][CH2:37][CH2:36][O:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:6][C@H:7]3[N:18]([C:19]([O:21][CH2:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[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

Participants

Conditions

Temperature: 50 °C

Procedure

To a stirred solution of 3-hydroxy-N-(benzyloxycarbonyl)morphinan 26 (3.6 mg, 0.009 mmol) in dry DMF (0.16 mL) were added potassium carbonate (4 mg, 0.028 mmol), 1-bromo-3-chloropropane (2.8 μL, 0.028 mmol) sequentially and the mixture was stirred at 50° C. After starting material disappeared on TLC, solvent was removed and column chromatography gave 3 mg (70%) of the title compound: 1H NMR (300 MHz, CDCl3) δ7.30 (5H, m); 7.00 (1H, t); 6.83 (1H, d); 6.70 (1H, d. d.); 5.10 (2H, m); 4.30 (1H, m); 4.05 (2H, t); 3.90 (1H, m); 3.79 (2H, t); 3.05 (1H, m); 2.75 (2H, m); 2.30 (1H, m); 2.15 (2H, m); 1.00˜1.80 (10H, m).

Workup

customwas removed

Sources & evidence

ORD record: ord-34487ad975a5461ca34f670ab32d4ae1
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07691874B2

Reaction notes

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