Methyl iodide → HCID 22708766, compound

HRID 351156Notes

Reaction equation

HRID 351156 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:18]=1[NH:17][CH2:16][CH2:15][CH2:14]2)=[O:7])([CH3:4])([CH3:3])[CH3:2].CI.[C:21]([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:21][N:17]1[C:18]2[C:13](=[CH:12][CH:11]=[CH:10][C:9]=2[NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:14][CH2:15][CH2:16]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 516892Sodium BicarbonateHCID 15092363HCID 15092363, compound

Product 1

HCID 22708766HCID 22708766, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 8-(N-tert-butoxycarbonylamino)-1,2,3,4-tetrahydroquinoline (0.876 g, 3.52 mmol) in CH2Cl2 (35 mL), at room temperature was added excess methyl iodide (2 mL, 32.12 mmol). The mixture was stirred at room temperature for 48 hours. The mixture was poured into saturated aqueous NaHCO3 (25 mL) and diluted with CH2Cl2 (25 mL). The phases were separated and the aqueous phase was extracted with CH2Cl2 (3×25 mL). The combined organic extracts were dried (Na2SO4) and concentrated. Purification of the crude material by flash chromatography (36 g silica gel, 10:1 hexanes-ethyl acetate) provided 0.83 g (90%) of 1-methyl-8-(N-tert-butoxycarbonylamino)-1,2,3,4-tetrahydroquinoline as a colorless oil. 1H NMR (CDCl3) δ 1.53 (s, 9H), 1.84–1.92 (m, 2H), 2.62 (s, 3H), 2.79 (t, 2H, J=6.6 Hz), 3.03–3.07 (m, 2H), 6.73 (d, 1H, J=7.8 Hz), 6.95 (dd, 1H, J=7.8, 7.8 Hz), 7.18 (br s, 1H, NH), 7.82 (br d, 1H, J=7.8 Hz).

Workup

  1. customThe phases were separated
  2. extractionthe aqueous phase was extracted with CH2Cl2 (3×25 mL)
  3. dry with materialThe combined organic extracts were dried (Na2SO4)
  4. concentrationconcentrated
  5. customPurification of the crude material by flash chromatography (36 g silica gel, 10:1 hexanes-ethyl acetate)

Sources & evidence

ORD record
ord-d74db8ca5270492b863184bddbe79315
Source dataset
uspto-grants-2007_02
Patent number
US07183273B2

Reaction notes

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