Benzyl Bromide → Tert-butyl 1-benzyl-1,2,3,4-tetrahydroquinolin-3-ylcarbamate

HRID 1158805Notes

Reaction equation

HRID 1158805 reaction equation
[C:1]([O:5][C:6](=[O:18])[NH:7][CH:8]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH2:25](Br)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C(O)C>[CH2:25]([N:10]1[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:17][CH:8]([NH:7][C:6](=[O:18])[O:5][C:1]([CH3:4])([CH3:2])[CH3:3])[CH2:9]1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 4460996Boc-3-amino-1,2,3,4-tetrahydroquinoline

Product 1

HCID 67236612Tert-butyl 1-benzyl-1,2,3,4-tetrahydroquinolin-3-ylcarbamateYield 77%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of (1,2,3,4-tetrahydroquinolin-3-yl)-carbamic acid tert-butyl ester (507 mg, 2.04 mmol) and potassium carbonate (367 mg, 2.65 mmol) in ethanol (15 mL) was treated with benzyl bromide (367 mg, 2.14 mmol)and stirred overnight at ambient temperature. The reaction mixture was partitioned between ethyl acetate (100 mL) and water (100 mL). The isolated organic phase was washed with brine and dried over anhydrous sodium sulfate, filtered and concentrated. The resulting oil was chromatographed on silica gel, eluting with 5-to-50% ethyl acetate in hexane to afford the title compound (529 mg, 77%) as a white solid. 1H NMR (300 MHz, DMSO-d6) δ:1.38 (s, 9H), 2.65-2.75 (dd, 1H), 2.83-2.92 (dd, 1H), 3.11-3.22 (dd, 1H), 3.35-3.42 (dd, 1H), 3.77-3.90 (m, 1H), 4.39-4.51 (q, 2H), 6.45-6.52 (m, 2H), 6.82-6.94 (m, 3H), 7.20-7.34 (m, 5H). MS (ESI) m/z 222.2, 283.1, 339.1 (M+H)+.

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate (100 mL) and water (100 mL)
  2. washThe isolated organic phase was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe resulting oil was chromatographed on silica gel
  7. washeluting with 5-to-50% ethyl acetate in hexane

Sources & evidence

ORD record
ord-96ed34882299404aa2efe753e4617cd1
Source dataset
uspto-grants-2010_10
Patent number
US07812019B2

Reaction notes

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