Potassium Hydroxide → 1,2-Pyrrolidinedicarboxylic acid, 3-hydroxy-, 1-(1,1-dimethylethyl) 2-methyl ester, (2R,3S)-rel-

HRID 751027노트

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HRID 751027 반응식
[CH3:1][O:2][C:3]([C@@H:5]1[C@H:9]([O:10]C(=O)C2C=CC=CC=2)[CH2:8][CH2:7][N:6]1[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[O:4].[OH-].[K+]>CO>[CH3:1][O:2][C:3]([C@@H:5]1[C@H:9]([OH:10])[CH2:8][CH2:7][N:6]1[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[O:4]

참가 물질

4

반응물 2

HCID 14797Potassium HydroxideHCID 58583618(2S,3R)-N-tert-Butoxycarbonyl-3-benzoyloxy-2-pyrrolidinecarboxylic acid methyl ester

생성물 1

HCID 109885451,2-Pyrrolidinedicarboxylic acid, 3-hydroxy-, 1-(1,1-dimethylethyl) 2-methyl ester, (2R,3S)-rel-수율 71.9%

시약·촉매·용매 1

HCID 887Methanol용매2회

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온도
0 °C

실험 절차

To a solution of compound 1C (88.44 g, 0.253 mol) in anhydrous MeOH (700 mL) cooled to 0° C. was slowly added a freshly prepared 1N solution of KOH in anhydrous MeOH (367 mL, 0.367 mol) over 25 min through an addition funnel. After the addition, the light yellow solution was stirred at 0° C. for 2 h, and then the reaction was quenched by slow addition (over 25 min) of a solution of 1N HCl in dioxane/EtOAc (380 mL) through an addition funnel. The resulting white suspension was concentrated under reduced pressure to remove most of the solvent, and the remaining mixture was partitioned between water and EtOAc. The separated organic phase was washed with water (2×), saturated aqueous NaHCO3 (2×), water, brine, and then dried (Na2SO4). The filtrate was concentrated under reduced pressure to give a light yellow oily residue, which was chromatographed (silica gel) eluting first with 25-30% EtOAc/hexane, then 5% MeOH in 30% EtOAc/hexane to furnish compound 1D (44.6 g) as a pale yellow oil.

후처리

  1. additionAfter the addition
  2. customthe reaction was quenched by slow addition (over 25 min) of a solution of 1N HCl in dioxane/EtOAc (380 mL) through an addition funnel
  3. concentrationThe resulting white suspension was concentrated under reduced pressure
  4. customto remove most of the solvent
  5. customthe remaining mixture was partitioned between water and EtOAc
  6. washThe separated organic phase was washed with water (2×), saturated aqueous NaHCO3 (2×), water, brine
  7. dry with materialdried (Na2SO4)
  8. concentrationThe filtrate was concentrated under reduced pressure
  9. customto give a light yellow oily residue, which
  10. customwas chromatographed (silica gel)
  11. washeluting first with 25-30% EtOAc/hexane

출처 및 근거

ORD 기록
ord-ada2e77324a945fc90dc45756e6bf30b
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07405234B2

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