Trimethylsilyl iodide → (S)-1-(5-Fluoropyridin-2-yl)ethanamine

HRID 1641398Notes

Reaction equation

HRID 1641398 reaction equation
C([C@@H]1CC[C@@H](C)C[C@H]1[N:11]([C@H:15]([C:17]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][N:18]=1)[CH3:16])C(=O)[O-])(C)C.[Si](I)(C)(C)C>C(Cl)(Cl)Cl>[F:23][C:20]1[CH:21]=[CH:22][C:17]([C@@H:15]([NH2:11])[CH3:16])=[N:18][CH:19]=1

Participants

4

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 86624812HCID 86624812, compound

Product 1

HCID 16097531(S)-1-(5-Fluoropyridin-2-yl)ethanamineYield 79%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

(1R,2S,5R)-2-Isopropyl-5-methylcyclohexyl [(1S)-1-(5-fluoropyridin-2-ypethyl]carbamate (Method 5; 3.0 g, 9.3 mmol) and TMSI (2.7 ml, 18.6 mmol) in chloroform (10 ml) was heated at 68° C. for 24 hours. Ice water (15 ml) was added carefully and extracted with ether (2×100 ml). The aqueous layer was separated, neutralized with solid sodium bicarbonate to PH=9 and extracted with ether (5×200 ml). The combined organic was dried over sodium sulfate and concentrated to give the title compound (1.03 g, 79%) as pale yellow oil. 1H NMR (400 MHz) 8.44 (d, J=2.8 Hz, 1H), 7.66 (ddd, J=2.8, 2.8 and 2.8 Hz, 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. extractionextracted with ether (2×100 ml)
  2. customThe aqueous layer was separated
  3. extractionextracted with ether (5×200 ml)
  4. dry with materialThe combined organic was dried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-2078d06c323f4257ba5e1ab27e0ced81
Source dataset
uspto-grants-2012_02
Patent number
US08114989B2

Reaction notes

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