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 1) (2.20 g, 7.08 mmol) was placed in a flask with dry THF (100 ml). This was cooled to 0° C. and lithium aluminum hydride (0.537 g, 14.16 mmol) was added. The reaction mixture was stirred at RT 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 were filtered off through Celite® (filter material) and the filtrate was partitioned between EtOAc and water. The organic phase was washed with water and brine, dried over MgSO4, filtered and the solvent was removed in vacuo to afford the title product which was 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). [M+H]+283.30.
Workup
- customquenched with water (0.5 ml), 2M NaOH (0.5 ml)
- filtrationThe solids were filtered off through Celite® (filter material)
- customthe filtrate was partitioned between EtOAc and water
- washThe organic phase was washed with water and brine
- dry with materialdried over MgSO4
- filtrationfiltered
- customthe solvent was removed in vacuo
Sources & evidence
- ORD record
- ord-879223f3a96b41aa862f75d5c89b826d
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08835444B2
Reaction notes
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