Water → HCID 53392445, compound

HRID 1922398Notes

Reaction equation

HRID 1922398 reaction equation
[N:1]1([CH:11]2[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12]2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.C1C(=O)N([Br:30])C(=O)C1.O>CN(C=O)C>[Br:30][C:7]1[CH:6]=[C:5]2[C:10](=[CH:9][CH:8]=1)[N:1]([CH:11]1[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12]1)[CH2:2][CH2:3][CH2:4]2

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 53392350HCID 53392350, compound

Product 1

HCID 53392445HCID 53392445, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of tert-butyl 3-(3,4-dihydroquinolin-1(2H)-yl)pyrrolidine-1-carboxylate (1.86 g, 6.15 mmol) in 15 mL of DMF was cooled to 0° C. then treated dropwise with NBS (1.09 g, 6.15 mmol) in 15 mL DMF. The reaction was stirred at 0° C. for 1.5 hours then treated with 100 mL H2O. The suspension was extracted with 2×150 mL EtOAc. The combined organic layer was rinsed with brine (3×20 mL), dried over Na2SO4, filtered and concentrated to give a viscous oil. This residue was subjected to flash chromatography on silica gel using 15% EtOAc/Hexanes to give a viscous oil (1.50 g, 63.8%). 1H-NMR (CDCl3) δ 7.13 (d, J=9.0 Hz, 1H), 7.07 (brs, 1H), 6.55 (d, J=9.0 Hz, 1H), 4.35-4.33 (m, 1H), 3.58-3.18 (m, 6H), 2.71 (t, J=6.3 Hz, 2H), 2.11-2.04 (m, 2H), 1.91-1.87 (m, 2H), 1.47 (s, 9H). MS (ESI): 325.1 and 327.1 (M+1, 100%).

Workup

  1. extractionThe suspension was extracted with 2×150 mL EtOAc
  2. washThe combined organic layer was rinsed with brine (3×20 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a viscous oil

Sources & evidence

ORD record
ord-b0b0a66f5ea04f038e5fd66d48ac0afd
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

Loading…