Aluminium lithium hydride → (4-(4-phenylthiazol-2-yl)tetrahydro-2H-pyran-4-yl)methanamine

HRID 1397205Notes

Reaction equation

HRID 1397205 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[C:7]1([C:13]2[N:14]=[C:15]([C:18]3([C:24]#[N:25])[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)[S:16][CH:17]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>C1COCC1>[C:7]1([C:13]2[N:14]=[C:15]([C:18]3([CH2:24][NH2:25])[CH2:19][CH2:20][O:21][CH2:22][CH2:23]3)[S:16][CH:17]=2)[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 673223044-(4-phenylthiazol-2-yl)tetrahydro-2H-pyran-4-carbonitrile

Product 1

HCID 67322930(4-(4-phenylthiazol-2-yl)tetrahydro-2H-pyran-4-yl)methanamineYield 37.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of LiAlH4 (220 mg, 5.9 mmol) in dry THF (10 mL) was added a solution of 4-(4-phenylthiazol-2-yl)tetrahydro-2H-pyran-4-carbonitrile (400 mg, 1.47 mmol) in dry THF (10 mL) at 0° C. The reaction mixture was stirred at room temperature for 1 h and then quenched carefully with water and diluted with EtOAc. The organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography (neutral alumina, eluent 5% MeOH in CHCl3) to afford (4-(4-phenylthiazol-2-yl)tetrahydro-2H-pyran-4-yl)methanamine (150 mg, yield 37%): 1H NMR (400 MHz, CDCl3) δ 7.89-7.91 (m, 2H), 7.48 (s, 1H), 7.33-7.46 (m, 3H), 3.89-3.93 (m, 2H), 3.63-3.69 (m, 2H), 3.03 (s, 2H), 2.30-2.33 (m, 2H), 1.90-1.97 (m, 2H). MS (ESI) m/z: Calculated for C15H18N2OS: 274.11. found: 275.2 (M+H)+.

Workup

  1. customquenched carefully with water
  2. additiondiluted with EtOAc
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography (neutral alumina, eluent 5% MeOH in CHCl3)

Sources & evidence

ORD record
ord-90fae064534f48718373221d1bf62b85
Source dataset
uspto-grants-2014_12
Patent number
US08901156B2

Reaction notes

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