Aluminium lithium hydride → (4-Benzylamino-3-methyl-cyclohexyl)-methanol

HRID 2391022Notes

Reaction equation

HRID 2391022 reaction equation
C([O:3][C:4]([CH:6]1[CH2:11][CH2:10][CH:9]([NH:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:8]([CH3:20])[CH2:7]1)=O)C.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH2:13]([NH:12][CH:9]1[CH2:10][CH2:11][CH:6]([CH2:4][OH:3])[CH2:7][CH:8]1[CH3:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 574659114-Benzylamino-3-methyl-cyclohexanecarboxylic acid ethyl ester

Product 1

HCID 67185026(4-Benzylamino-3-methyl-cyclohexyl)-methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A cooled (0° C.) mixture comprising 4-benzylamino-3-methyl-cyclohexanecarboxylic acid ethyl ester (0.90 g, 3.27 mmol) in THF (50 mL) is treated with LiAlH4 (4.09 mL, 8.08 mmol of a 2M solution in THF) and the reaction mixture is stirred at RT for 2 hours. The reaction is quenched with water (5 mL), NaOH (5 mL) followed by water (20 mL). The resulting precipitate is removed by filtration and washed with EtOAc. The organic phase is washed with water, brine, dried (MgSO4) and concentrated in vacuo to afford the title compound which is used in the next step without further purification. 1H NMR (400 MHz, DMSO-d6) δ 7.30 (4H, m), 7.19 (1H, m) 4.31 (1H, t), 3.68 (2H, m), 3.29 (0.4H, t), 3.15 (1.6H, t), 2.45 (1H, m), 2.18 (0.2H, m), 2.06 (0.8H, m), 1.69 (2H, m), 1.52 (3H, m), 1.27 (2H, m), 1.03 (1H, m), 0.90 (0.6H, d), 0.88 (2.4H, d), 0.80 (1H, m).

Workup

  1. customThe reaction is quenched with water (5 mL), NaOH (5 mL)
  2. customThe resulting precipitate is removed by filtration
  3. washwashed with EtOAc
  4. washThe organic phase is washed with water, brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1f0a36953307471886a8f62af153d6c7
Source dataset
uspto-grants-2012_09
Patent number
US08273900B2

Reaction notes

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