1,4-Dioxane hydrochloride → (1S)-1-(5-Bromopyridin-2-yl)ethan-1-amine

HRID 1641407Notes

Reaction equation

HRID 1641407 reaction equation
C(OC(=O)[NH:7][C@H:8]([C:10]1[CH:15]=[CH:14][C:13]([Br:16])=[CH:12][N:11]=1)[CH3:9])(C)(C)C.Cl.O1CCOCC1>C(Cl)Cl>[Br:16][C:13]1[CH:14]=[CH:15][C:10]([C@@H:8]([NH2:7])[CH3:9])=[N:11][CH:12]=1

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 904516721,1-Dimethylethyl N-[(1S)-1-(5-bromo-2-pyridinyl)ethyl]carbamate

Product 1

HCID 50999176(1S)-1-(5-Bromopyridin-2-yl)ethan-1-amineYield 73.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-tert-butyl-1-(5-bromopyridin-2-yl)ethylcarbamate (Method 27; 2.0 g, 6.6 mmol) in DCM (15 ml) was added HCl/dioxane (17 ml, 4 N, 68 mmol). The reaction was stirred at room temperature for 1 hour. The solvent was removed and 10 ml of saturated sodium bicarbonate was added. The resulting aqueous solution was extracted with ether (6×100 ml), dried over sodium sulfate and concentrated to give the title compound (0.98 g, 73%) as a pale yellow oil. 1H NMR (400 MHz, CDCl3) δ 8.60 (d, J=1.2 Hz, 1H), 7.76 (dd, J=2.0 and 8.4 Hz, 1H), 7.24 (d, J=8.0 Hz, 1H), 4.13 (q, J=6.8 Hz, 1H), 1.73 (b, 2H), 1.41 (d, J=6.4 Hz, 3H).

Workup

  1. customThe solvent was removed
  2. addition10 ml of saturated sodium bicarbonate was added
  3. extractionThe resulting aqueous solution was extracted with ether (6×100 ml)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-9775f27cfdec44a6ae379ed74a6cb9c3
Source dataset
uspto-grants-2012_02
Patent number
US08114989B2

Reaction notes

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