Aluminium lithium hydride → HCID 178432775、化合物

HRID 2391029ノート

反応式

HRID 2391029 の反応式
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]

参加物

4

反応物 2

HCID 21226445Aluminium lithium hydrideHCID 178501231HCID 178501231、化合物

生成物 1

HCID 178432775HCID 178432775、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  1. customquenched with water (0.5 mL), 2M NaOH (0.5 mL)
  2. filtrationThe solids are filtered off through Celite® (filter material)
  3. customthe filtrate is partitioned between EtOAc and water
  4. washThe organic phase is washed with water and brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customthe solvent is removed in vacuo

出典と根拠

ORDレコード
ord-0936d4dab61e45f8b63d47c3224ee42e
出典データセット
uspto-grants-2012_09
特許番号
US08273900B2

反応ノート

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