Imidazole → 1-(Phenylmethyl) (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate

HRID 50139

반응식

HRID 50139 반응식
C[O:2][C:3](=[O:17])[C@@H:4]1[CH2:8][C@@H:7]([OH:9])[CH2:6][N:5]1[C:10]([O:12][C:13]([CH3:16])(C)C)=[O:11].N1[CH:22]=[CH:21]N=C1.[Si](Cl)([C:26](C)([CH3:28])[CH3:27])(C)C>CN(C=O)C>[OH:9][C@H:7]1[CH2:6][N:5]([C:10]([O:12][CH2:13][C:16]2[CH:22]=[CH:21][CH:28]=[CH:26][CH:27]=2)=[O:11])[C@H:4]([C:3]([OH:2])=[O:17])[CH2:8]1

참가 물질

5

반응물 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 2734883(2S,4R)-4-Hydroxypyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

생성물 1

HCID 3915171-(Phenylmethyl) (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate수율 120.9%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Boc-trans-4-hydroxy-L-proline methyl ester (10.35 g, 0.04 mol) was dissolved in DMF (135 mL). Imidazole (13.6 g, 0.20 mol) was added, followed by the addition of tert-butyldimethylsilyl chloride (18.1 g, 0.12 mol) and the solution was stirred overnight at room temperature. DMF was removed via vacuum rotary evaporation and the residue was dissolved in ethyl acetate. The solution was washed with 1M HCl and brine. The organic solution was dried over MgSO4 and concentrated. The crude product was purified by column chromatography eluting with hexanes/ethyl acetate (4/1, v/v) to afford 12.83 g (89% yield) of the desired product 1 as a colorless oil.

후처리

  1. customDMF was removed via vacuum rotary evaporation
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washThe solution was washed with 1M HCl and brine
  4. dry with materialThe organic solution was dried over MgSO4
  5. concentrationconcentrated
  6. customThe crude product was purified by column chromatography
  7. washeluting with hexanes/ethyl acetate (4/1

출처 및 근거

ORD 기록
ord-3e46b3c321194f89bb9fffbafd080b0b
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06710186B2

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