1-Bromo-3-chloropropane → HCID 68576672, compound

HRID 639518Notes

Reaction equation

HRID 639518 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(=O)([O-])[O-].[K+].[K+].Br[CH2:33][CH2:34][CH2:35][Cl:36]>CN(C=O)C>[Cl:36][CH2:35][CH2:34][CH2:33][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

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 59254973HCID 59254973, compound

Product 1

HCID 68576672HCID 68576672, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred solution of 3-hydroxy-N-(tert-butyloxycarbonyl)morphinan (20 mg, 0.058 mmol) in dry DMF (0.3 mL) was added potassium carbonate (24 mg, 0.174 mmol), 1-bromo-3-chloropropane (17.3 μL, 0.174 mmol) sequentially and the mixture was stirred at 50° C. After starting material disappeared on TLC, solvent was removed and column chromatography gave 18 mg (74%) of the title compound: 1H NMR (300 MHz, CDCl3) δ 7.05 (1H, m); 6.83 (1H, d); 6.75 (1H, d.d.); 4.28 (1H, d); 4.05 (2H, t); 3.90 (1H, m); 3.83 (3H, t); 3.15 (1H, m); 2.60 (2H, m); 2.30 (1H, m); 2.15 (1H, m); 1.30 (9H, s); 1.00˜1.80 (10H, m).

Workup

  1. customwas removed

Sources & evidence

ORD record
ord-b6e420f595b544ceb448506e50eba5d5
Source dataset
uspto-grants-2010_04
Patent number
US07691874B2

Reaction notes

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