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

HRID 50139

反応式

HRID 50139 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-3e46b3c321194f89bb9fffbafd080b0b
出典データセット
uspto-grants-2004_03
特許番号
US06710186B2

関連ノート

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