Aluminium lithium hydride → HCID 178432775, 화합물

HRID 75517노트

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HRID 75517 반응식
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]

참가 물질

4

반응물 2

HCID 21226445Aluminium lithium hydrideHCID 178501231HCID 178501231, 화합물

생성물 1

HCID 178432775HCID 178432775, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-879223f3a96b41aa862f75d5c89b826d
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08835444B2

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