1-(Phenylmethyl) (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate → Benzyl (2S,4R)-4-hydroxy-2-(hydroxymethyl)pyrrolidine-1-carboxylate

HRID 37027

反応式

HRID 37027 の反応式
[C:1]([N:11]1[CH2:19][C@H:17]([OH:18])[CH2:16][C@H:12]1[C:13](O)=[O:14])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2]>C1COCC1>[CH2:4]([O:3][C:1]([N:11]1[CH2:19][C@H:17]([OH:18])[CH2:16][C@H:12]1[CH2:13][OH:14])=[O:2])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

参加物

3

反応物 1

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

生成物 1

HCID 14994791Benzyl (2S,4R)-4-hydroxy-2-(hydroxymethyl)pyrrolidine-1-carboxylate収率 48.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To an ice cold solution of 4.76 g (18 mmoles) of CBZ hydroxyproline (Sigma Chemical Co.) in 20 mL of dry THF was added 45 mL of a 1M solution borane-THF complex in THF (Aldrich). After stirring under argon for 15 min at 0°-5° C., and 4.5 h at room temperature, the mixture was quenched with 50 mL of methanol. After 30 min, the solution was concentrated. The residual colorless syrup was purified by flash chromatography (3.5×23 cm silica) using a gradient of methanol in methylene chloride. The product eluted with 10% methanol. The fractions containing pure product were stripped of solvent to give 2.18 g (46% yield) of 1 as a colorless syrup.

後処理

  1. custom4.5 h at room temperature, the mixture was quenched with 50 mL of methanol
  2. waitAfter 30 min
  3. concentrationthe solution was concentrated
  4. customThe residual colorless syrup was purified by flash chromatography (3.5×23 cm silica)
  5. washThe product eluted with 10% methanol
  6. additionThe fractions containing pure product

出典と根拠

ORDレコード
ord-673dcebd3c1f4bf982f5647338d23688
出典データセット
uspto-grants-1995_05
特許番号
US05419966

関連ノート

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