Aluminium lithium hydride → 1-ethyl-3-[2-(1-pyrrolidinyl)ethyl]-1H-pyrazol-5-amine

HRID 62499Notes

Reaction equation

HRID 62499 reaction equation
[CH2:1]([N:3]1[C:7]([NH2:8])=[CH:6][C:5]([CH2:9][C:10](=O)[N:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)=[N:4]1)[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3]>O1CCCC1>[CH2:1]([N:3]1[C:7]([NH2:8])=[CH:6][C:5]([CH2:9][CH2:10][N:11]2[CH2:12][CH2:13][CH2:14][CH2:15]2)=[N:4]1)[CH3:2]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 575169011-ethyl-3-[2-oxo-2-(1-pyrrolidinyl)ethyl]-1H-pyrazol-5-amine

Product 1

HCID 575169001-ethyl-3-[2-(1-pyrrolidinyl)ethyl]-1H-pyrazol-5-amineYield 59.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-ethyl-3-[2-oxo-2-(1-pyrrolidinyl)ethyl]-1H-pyrazol-5-amine (600 mg, 1.784 mmol) in tetrahydrofuran (8 mL) cooled with water-ice bath was added a solution of 2M LAH (1.0 mL, 2.00 mmol) solution dropwise, and the reaction mixture was stirred for 5 h at rt and 30 min at 50 degree. The reaction mixture was carefully quenched with methanol followed by water and concentrated. The residue was washed with DCM/methanol 5 times. The extract was concentrated and the residue was purified using HPLC under the basic conditions to give 220 mg of product. MS: (M+H)+=208.7. 1H NMR (400 MHz, CHLOROFORM-d) ppm 1.37 (t, J=7.2 Hz, 3H), 1.79 (m, 4H), 2.56 (m, 4H), 2.71 (m, 2H), 3.42 (m, 2H), 3.94 (q, J=7.2 Hz, 2H), 5.40 (s, 1H).

Workup

  1. customThe reaction mixture was carefully quenched with methanol
  2. concentrationconcentrated
  3. washThe residue was washed with DCM/methanol 5 times
  4. concentrationThe extract was concentrated
  5. customthe residue was purified

Sources & evidence

ORD record
ord-ef0183a0545144c3b282e4ff88754e48
Source dataset
uspto-grants-2016_09
Patent number
US09446034B2

Reaction notes

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