Ammonium Hydroxide → (3R,4R)-1-Benzylpyrrolidine-3,4-diol

HRID 1723708노트

반응식

HRID 1723708 반응식
[CH2:1]([N:8]1[C:12](=O)[C@@H:11]([OH:14])[C@H:10]([OH:15])[C:9]1=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.COC(C)[O-].COC(C)[O-].[H-].[Al+3].[Na+].COCCO[AlH2-]OCCOC.[Na+].[OH-].[NH4+]>C1COCC1.C(Cl)Cl.CCOC(C)=O.C1(C)C=CC=CC=1>[CH2:1]([N:8]1[CH2:12][C@@H:11]([OH:14])[C@H:10]([OH:15])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

9

반응물 4

HCID 14923Ammonium HydroxideHCID 729944HCID 729944, 화합물HCID 16684438Red-AlHCID 131727259HCID 131727259, 화합물

생성물 1

HCID 7021491(3R,4R)-1-Benzylpyrrolidine-3,4-diol

시약·촉매·용매 4

HCID 1140Toluene용매HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

To a mechanically stirred and cooled solution (0° C.) of the product from Step 1 (50 g, 0.23 mol) in dry THF (1.24 L) was added sodium aluminum hydride bis-(methoxyethoxide) (289 mL of a 65% Red-Al®/Toluene solution, 0.95 mol) under a nitrogen atmosphere at such a rate that the internal temperature did not exceed 20° C. The reaction mixture was allowed stir at room temperature for 2 h after the addition was complete. The reaction mixture was slowly poured into ice water (1.0 L) with stirring to quench the reaction. After warming to room temperature, 30% ammonium hydroxide (100 mL) was added followed by EtOAc (1.5 L) and this mixture was stirred for 16 h. The suspension was filtered through diatomaceous earth and the solids were washed with EtOAc. The filtrate layers were separated and the organic phase was dried over sodium sulfate and concentrated to afford a syrup. Dissolution in methylene chloride and concentration affords a white solid that is collected and dried (43.7 g, 86%). 1H NMR (300 MHz, CDCl3) δ 7.36-7.23 (5H, m), 6.23 (2H, m), 4.65 (1H, m), 4.15-4.00 (3H, m), 3.62-3.49 (1H, dd), 3.33 (1H, dd), 3.14 (1H, dd), 2.94 (1H dd). MS m/z 194 (MH+).

후처리

  1. customdid not exceed 20° C
  2. stirringThe reaction mixture was allowed stir at room temperature for 2 h
  3. additionafter the addition
  4. stirringwith stirring
  5. customto quench
  6. customthe reaction
  7. stirringthis mixture was stirred for 16 h
  8. filtrationThe suspension was filtered through diatomaceous earth
  9. washthe solids were washed with EtOAc
  10. customThe filtrate layers were separated
  11. dry with materialthe organic phase was dried over sodium sulfate
  12. concentrationconcentrated
  13. customto afford a syrup
  14. concentrationconcentration
  15. customaffords a white solid
  16. customthat is collected
  17. customdried (43.7 g, 86%)

출처 및 근거

ORD 기록
ord-3582ce71857b41a1923e2d2db1fb4b32
출처 데이터셋
uspto-grants-2009_02
특허 번호
US07485641B2

반응 노트

불러오는 중…