Nitrogen → HCID 59536627, 화합물

HRID 1922181노트

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HRID 1922181 반응식
N#N.[CH2:3]([N:10]1[CH2:14][CH2:13][C@H:12]([C@@H:15]([OH:20])[CH2:16][CH:17]([CH3:19])[CH3:18])[C:11]1=O)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.COCCO[AlH2-]OCCOC.[Na+]>C1(C)C=CC=CC=1>[CH2:3]([N:10]1[CH2:14][CH2:13][C@H:12]([C@@H:15]([OH:20])[CH2:16][CH:17]([CH3:18])[CH3:19])[CH2:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

참가 물질

5

반응물 3

HCID 947NitrogenHCID 16684438Red-AlHCID 59536630(R)-1-benzyl-3-((S)-1-hydroxy-3-methylbutyl)pyrrolidin-2-one

생성물 1

HCID 59536627HCID 59536627, 화합물수율 101.5%

시약·촉매·용매 1

HCID 1140Toluene용매3회

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온도
0 °C

실험 절차

Charge a 1 L, 3-neck round bottom flask equipped with a magnetic stirrer, thermal couple, addition funnel and N2 inlet with crude (R)-1-benzyl-3-((S)-1-hydroxy-3-methylbutyl)pyrrolidin-2-one (38.26 mmoles, assumed) and toluene (100 mL). Cool the slightly heterogeneous stirring solution to 0° C. (salt/ice bath) and add a solution of Vitride™ (Rohm & Haas) (65 wt % in toluene, 24 mL, 86.085 mmoles) and toluene (70 mL) drop wise while maintaining a temperature at or below 5° C. Rinse the addition funnel with toluene (10-20 mL). Stir at room temperature overnight (˜16 hr). Cool the reaction mixture to 0° C. (salt/ice bath) and quenched with saturated Rochell's salt solution (200 mL) followed by MTBE (200 mL). Allow the mixture to warm to room temperature with stirring and then stir at this temperature for 1 hour. Separate the organic and aqueous layers and wash the organic layer with H2O (2×200 mL), then brine (200 mL), and then dry over Na2SO4. Filter and concentrate to give the desired intermediate as a brown oil (9.61 g, 38.85 mmoles, >100% yield). 1H NMR (300 MHz, CDCl3) δ 7.36-7.18 (m, 5H), 3.82-3.72 (m, 1H), 3.58 (dd, 2H, 7.61, 20.51 Hz), 2.87 (td, 1H, J=4.10, 8.79 Hz), 2.79-2.70 (m, 1H), 2.48-2.38 (m, 1H), 2.26-2.04 (m, 2H), 1.98-1.64 (m, 3H), 1.46-1.32 (m, 1H), 1.14-0.98 (m, 1H), 0.92 (d, 3H, J=1.18 Hz), 0.89 (d, 3H, J=1.76 Hz). LC/MS=248.1 (M+1).

후처리

  1. additionCharge a 1 L, 3-neck round bottom flask
  2. customequipped with a magnetic stirrer
  3. temperaturewhile maintaining a temperature at or below 5° C
  4. washRinse the addition funnel with toluene (10-20 mL)
  5. temperatureCool the reaction mixture to 0° C. (salt/ice bath)
  6. customquenched with saturated Rochell's salt solution (200 mL)
  7. temperatureAllow the mixture to warm to room temperature
  8. stirringwith stirring
  9. stirringstir at this temperature for 1 hour
  10. customSeparate the organic and aqueous layers
  11. washwash the organic layer with H2O (2×200 mL)
  12. dry with materialbrine (200 mL), and then dry over Na2SO4
  13. filtrationFilter
  14. concentrationconcentrate

출처 및 근거

ORD 기록
ord-d9e0156f5ec54e1b965030770d4bd5ac
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08173821B2

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