Aluminium lithium hydride → HCID 178432775, compound
Reaction equation
C[O:2][C:3]([C@H:5]1[CH2:10][CH2:9][C@H:8]([NH:11][C:12]([C:14]2[C:15]([CH3:21])=[N:16][CH:17]=[C:18]([Cl:20])[CH:19]=2)=[O:13])[CH2:7][CH2:6]1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[Cl:20][C:18]1[CH:17]=[N:16][C:15]([CH3:21])=[C:14]([CH:19]=1)[C:12]([NH:11][C@H:8]1[CH2:7][CH2:6][C@H:5]([CH2:3][OH:2])[CH2:10][CH2:9]1)=[O:13]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
Trans-4-[(5-Chloro-2-methyl-pyridine-3-carbonyl)-amino]-cyclohexanecarboxylic acid methyl ester (step 2) (2.20 g, 7.08 mmol) is placed in a flask with dry THF (100 mL). This is cooled to 0° C. and lithium aluminum hydride (0.537 g, 14.16 mmol) is added. The reaction mixture is stirred at r.t. for 2 hours and then quenched with water (0.5 mL), 2M NaOH (0.5 mL) and then water again (1.5 mL). The solids are filtered off through Celite® (filter material) and the filtrate is partitioned between EtOAc and water. The organic phase is washed with water and brine, dried over MgSO4, filtered and the solvent is removed in vacuo to afford the title product which is used in the next step without further purification. 1H NMR (400 MHz, DMSO-d6) δ 8.53 (1H, d), 8.38 *1H, d), 7.79 (1H, d), 4.40 (1H, t), 3.66 (1H, m), 3.21 (2H, t), 2.47 (3H, s), 1.92 (2H, m), 1.78 (2H, m), 1.31 (1H, m), 1.22 (2H, m), 0.98 (2H, m). [MH]+ 283.30.
Workup
- customquenched with water (0.5 mL), 2M NaOH (0.5 mL)
- filtrationThe solids are filtered off through Celite® (filter material)
- customthe filtrate is partitioned between EtOAc and water
- washThe organic phase is washed with water and brine
- dry with materialdried over MgSO4
- filtrationfiltered
- customthe solvent is removed in vacuo
Sources & evidence
- ORD record
- ord-0936d4dab61e45f8b63d47c3224ee42e
- Source dataset
- uspto-grants-2012_09
- Patent number
- US08273900B2
Reaction notes
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