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(5S)-5-(Hydroxymethyl)-1-methyl-2-pyrrolidinone → HCID 178481529, 화합물

HRID 82767
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HRID 82767 반응식
[OH:1][CH2:2][C@H:3]1[N:7]([CH3:8])[C:6](=[O:9])[CH2:5][CH2:4]1.CC(C)([O-])C.[Na+].[C:16]([C:20]1[S:24]/[C:23](=[N:25]\[C:26](=[O:38])[C:27]2[CH:32]=[C:31]([C:33]([F:36])([F:35])[F:34])[CH:30]=[CH:29][C:28]=2F)/[N:22]([CH2:39][C@H:40]2[CH2:44][CH2:43][CH2:42][O:41]2)[CH:21]=1)([CH3:19])([CH3:18])[CH3:17]>C1COCC1>[C:16]([C:20]1[S:24]/[C:23](=[N:25]\[C:26](=[O:38])[C:27]2[CH:32]=[C:31]([C:33]([F:35])([F:34])[F:36])[CH:30]=[CH:29][C:28]=2[O:1][CH2:2][C@@H:3]2[CH2:4][CH2:5][C:6](=[O:9])[N:7]2[CH3:8])/[N:22]([CH2:39][C@H:40]2[CH2:44][CH2:43][CH2:42][O:41]2)[CH:21]=1)([CH3:19])([CH3:17])[CH3:18]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 14876039(5S)-5-(Hydroxymethyl)-1-methyl-2-pyrrolidinoneHCID 23676156Sodium t-butoxideHCID 178441320HCID 178441320, 화합물

생성물 1

HCID 178481529HCID 178481529, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
22 °C

실험 절차

To a solution of (S)-5-(hydroxymethyl)-1-methylpyrrolidin-2-one (108 mg, 0.84 mmol) (Williams, P. D. et al. Journal of Medicinal Chemistry 1991, 34, 887-900) in 5 mL of THF was added sodium tert-butoxide (100 mg, 1.05 mmol). The mixture was stirred at 22° C. for 20 minutes. The mixture was cooled to 5° C. and a solution of Example 1A (180 mg, 0.42 mmol) in 2 mL of THF was added. The mixture was stirred at 5° C. for 2 hours, then at 22° C. for 1 hour. The solvent was evaporated under reduced pressure. The residue was dissolved in methylene chloride, washed with water, dried over MgSO4 and concentrated. The residue was purified by flash chromatography on SiO2 using an Analogix® Intelliflash280™ (eluted with CH2Cl2:10% MeOH and 3N NH3 in CH2Cl2: 0 to 100%) to afford the title compound; 1H NMR (300 MHz, CDCl3) δ ppm 1.36 (s, 9 H), 1.58-1.73 (m, 1 H), 1.74-2.14 (m, 4 H), 2.14-2.42 (m, 2 H), 2.44-2.64 (m, 1 H), 2.91 (s, 3 H), 3.72-3.91 (m, 2 H), 3.93-4.03 (m, 1H), 4.07 (dd, J=12.0, 4.8 Hz, 1 H), 4.14-4.32 (m, 3 H), 4.39 (dd, J=13.3, 2.6 Hz, 1 H), 6.88 (s, 1 H), 6.99 (d, J=8.7 Hz, 1 H), 7.60 (dd, J=8.7, 2.4 Hz, 1 H), 8.11 (d, J=2.4 Hz, 1 H); MS (ESI) m/z 540 (M+H)+.

후처리

  1. temperatureThe mixture was cooled to 5° C.
  2. stirringThe mixture was stirred at 5° C. for 2 hours
  3. waitat 22° C. for 1 hour
  4. customThe solvent was evaporated under reduced pressure
  5. dissolutionThe residue was dissolved in methylene chloride
  6. washwashed with water
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated
  9. customThe residue was purified by flash chromatography on SiO2 using
  10. washan Analogix® Intelliflash280™ (eluted with CH2Cl2:10% MeOH and 3N NH3 in CH2Cl2: 0 to 100%)

출처 및 근거

ORD 기록
ord-28e7ce224bf049129438164bfc38a0cc
출처 데이터셋
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08846730B2

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