Sodium borohydride → HCID 178479966、化合物

HRID 511244ノート

反応式

HRID 511244 の反応式
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([CH:13]2[CH2:18][CH2:17][C:16](=[O:19])[CH2:15][CH2:14]2)=[C:6]2[C:10]=1[C:9](=[O:11])[N:8]([CH3:12])[CH2:7]2.[BH4-].[Na+]>CO>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C@H:13]2[CH2:18][CH2:17][C@@H:16]([OH:19])[CH2:15][CH2:14]2)=[C:6]2[C:10]=1[C:9](=[O:11])[N:8]([CH3:12])[CH2:7]2

参加物

4

反応物 2

HCID 4311764Sodium borohydrideHCID 672561257-amino-2-methyl-4-(4-oxocyclohexyl)-2,3-dihydro-1H-isoindol-1-one

生成物 1

HCID 178479966HCID 178479966、化合物

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
0 °C

実験手順

A solution of 7-amino-2-methyl-4-(4-oxocyclohexyl)-2,3-dihydro-1H-isoindol-1-one (1.35 g, 5.23 mmol) was dissolved in MeOH (30 mL), and cooled to 0° C., followed by addition of sodium borohydride (0.198 g, 5.23 mmol). The reaction mixture was stirred at 0° C. for 1 h. The reaction was quenched with sat. aq. NH4Cl, diluted with EtOAc, washed with brine, and dried over anhydrous sodium sulfate. The compound was purified on an Isco Combiflash eluting with 0 to 4% MeOH in EtOAc to afford the trans isomer and the cis isomer. Trans-isomer: 1H NMR (400 MHz, DMSO-d6) δ 7.05 (d, J=8.34 Hz, 1H), 6.51 (d, J=8.34 Hz, 1H), 5.83 (s, 2H), 4.53 (d, J=4.29 Hz, 1H), 4.33 (s, 2H), 3.38-3.48 (m, 1H), 2.98 (s, 3H), 2.28-2.38 (m, 1H), 1.90 (d, J=9.35 Hz, 2H), 1.68 (d, J=12.38 Hz, 2H), 1.38-1.51 (m, 2H), 1.19-1.32 (m, 2H); MS (ES+): m/z: 262.1674 [MH+]. HPLC: tR=0.98 min (UPLC TOF MS: polar—3 min). Cis-isomer: 1H NMR (400 MHz, DMSO-d6) δ 7.07 (d, J=8.34 Hz, 1H), 6.54 (d, J=8.34 Hz, 1H), 5.83 (s, 2H), 4.33 (s, 3H), 2.99 (s, 3H), 2.34-2.43 (m, 1H), 1.70-1.87 (m, 4H), 1.38-1.57 (m, 4H); MS (ES+): m/z: 262.1693 [MH+]. HPLC: tR=1.04 min (UPLC TOF MS: polar—3 min).

後処理

  1. customThe reaction was quenched with sat. aq. NH4Cl
  2. additiondiluted with EtOAc
  3. washwashed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe compound was purified on an Isco Combiflash
  6. washeluting with 0 to 4% MeOH in EtOAc
  7. customto afford the trans isomer
  8. customHPLC: tR=0.98 min (UPLC TOF MS: polar—3 min)
  9. customHPLC: tR=1.04 min (UPLC TOF MS: polar—3 min)

出典と根拠

ORDレコード
ord-d249c05f49a5472fa01eafe13c59ec57
出典データセット
uspto-grants-2015_08
特許番号
US09096624B2

反応ノート

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