Sodium borohydride → HCID 178479966, 화합물

HRID 511244노트

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HRID 511244 반응식
[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

참가 물질

4

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

생성물 1

HCID 178479966HCID 178479966, 화합물

시약·촉매·용매 1

HCID 887Methanol용매

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온도
0 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-d249c05f49a5472fa01eafe13c59ec57
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09096624B2

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