1,4-Dioxane hydrochloride → (S)-1-(5-fluoropyridin-2-yl)ethanamine hydrochloride

HRID 450356Notes

Reaction equation

HRID 450356 reaction equation
C(OC(=O)[NH:7][C@H:8]([C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][N:11]=1)[CH3:9])(C)(C)C.[ClH:18].O1CCOCC1>ClCCl>[ClH:18].[F: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 71299175(S)-tert-Butyl (1-(5-fluoropyridin-2-yl)ethyl)carbamate2×

Product 1

HCID 67123789(S)-1-(5-fluoropyridin-2-yl)ethanamine hydrochlorideYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-Butyl[(1S)-1-(5-fluoropyridin-2-yl)ethyl]carbamate (Intermediate 4, 12.8 g, 53.3 mmol) in dichloromethane (100 ml) was added HCl/dioxane solution (107 ml, 4 N, 428 mmol). The reaction was stirred at room temperature for 3 hours. The solvent was removed and 50 ml of saturated sodium bicarbonate was added. The resulting aqueous solution was extracted with ether (6×400 ml), dried over sodium sulfate and concentrated to give the title compound (7.30 g, 98%) as pale yellow oil. 1H NMR (400 MHz) δ 8.44 (d, J=2.8 Hz, 1H), 7.66 (m, 1H), 7.53 (m, 1H), 4.01 (q, J=6.8 Hz, 1H), 1.94 (b, 2H), 1.26 (d, J=6.8 Hz, 3H). MS: Calcd.: 140. Found: [M+H]+ 141.

Workup

  1. customThe solvent was removed
  2. addition50 ml of saturated sodium bicarbonate was added
  3. extractionThe resulting aqueous solution was extracted with ether (6×400 ml)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-6a0dcbf9493143dfa5af6a9be115996b
Source dataset
uspto-grants-2013_07
Patent number
US08486966B2

Reaction notes

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