Tetrahydrofuran → HCID 58710047, compound

HRID 2375915Notes

Reaction equation

HRID 2375915 reaction equation
C(O[C:6]([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[CH:19]=[C:18]([N+:20]([O-])=O)[CH:17]=[CH:16][C:15]=2[F:23])[CH2:10][CH2:9]1)=O)(C)(C)C.C1COCC1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O>[F:23][C:15]1[CH:16]=[CH:17][C:18]([NH2:20])=[CH:19][C:14]=1[C:11]1[CH2:12][CH2:13][N:8]([CH3:6])[CH2:9][CH:10]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 21226445Aluminium lithium hydrideHCID 59854593HCID 59854593, compound

Product 1

HCID 58710047HCID 58710047, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A dried flask was charged with 4-(2-fluoro-5-nitrophenyl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (645 mg, 2.00 mmol) and THF (10 mL). Lithium aluminium hydride (1M in THF, 20 mL, 20.0 mmol) was added slowly through a syringe under N2 (the reaction was very exothermic). The resulting mixture was stirred for 16 h at rt. Water was cautiously added to quench the reaction. The resulting mixture was filtered, and the filtrate was concentrated to dryness to give the title compound as a brown oil. 1H NMR (DMSO-d6, 400 MHz): δ=2.14 (s, 3H), 2.38-2.44 (m, 2H), 2.89-2.90 (m, 2H), 3.22 (brs, 2H), 5.95 (brs, 1H), 7.24-7.29 (m, 1H), 7.67-7.73 (m, 2H), 8.16 (s, 1H). MS (ES+): m/z 206.26 (100) [MH+]. HPLC: tR=1.68 min (ZQ2000, polar—5 min).

Workup

  1. customto quench
  2. customthe reaction
  3. filtrationThe resulting mixture was filtered
  4. concentrationthe filtrate was concentrated to dryness

Sources & evidence

ORD record
ord-4829547dc8754a09ad2f53ebe306c7ef
Source dataset
uspto-grants-2008_12
Patent number
US07465726B2

Reaction notes

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