Glycine tert-butyl ester → 5-[(Tert-butoxycarbonylmethyl-amino)-methyl]-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester

HRID 71735

反応式

HRID 71735 の反応式
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[CH3:15][CH2:16][O:17][C:18]([CH:20]1[CH2:24][CH2:23][CH:22]([CH:25]=O)[N:21]1[C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])=[O:19].[C:34]([O:38][C:39](=[O:42])[CH2:40][NH2:41])([CH3:37])([CH3:36])[CH3:35]>ClCCl>[CH3:15][CH2:16][O:17][C:18]([CH:20]1[CH2:24][CH2:23][CH:22]([CH2:25][NH:41][CH2:40][C:39]([O:38][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:42])[N:21]1[C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])=[O:19]

参加物

5

反応物 3

HCID 151417Glycine tert-butyl esterHCID 5049666Sodium triacetoxyborohydrideHCID 723380465-Formyl-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester

生成物 1

HCID 666209305-[(Tert-butoxycarbonylmethyl-amino)-methyl]-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester収率 47.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Sodium triacetoxyborohydride (2.08 g, 9.86 mmol) was added to a solution of 5-formyl-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester (891 mg, 3.29 mmol) and glycine t-butyl ester (1.65 g, 9.86 mmol) in dichloromethane (20 mL) over 2 minutes—a small amount of gas evolution was observed. After 1 hour the reaction was quenched with saturated ammonium chloride (5 mL). The mixture was extracted with ethyl acetate (3×25 mL). The combined organic phases were dried over sodium sulfate, filtered and the solvent was removed under reduced pressure. The resulting residue was purified by flash chromatography with methanol and dichloromethane as the eluant at a gradient of 0-10%. The fractions containing product were combined and the solvent was removed under reduced pressure to provide 5-[(tert-butoxycarbonylmethyl-amino)-methyl]-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester (601 mg, 1.55 mmol, 47%). C19H34N2O6 calculated 386.2, observed [M+1]+ 387.2; rt=1.61 min.

後処理

  1. customAfter 1 hour the reaction was quenched with saturated ammonium chloride (5 mL)
  2. extractionThe mixture was extracted with ethyl acetate (3×25 mL)
  3. dry with materialThe combined organic phases were dried over sodium sulfate
  4. filtrationfiltered
  5. customthe solvent was removed under reduced pressure
  6. customThe resulting residue was purified by flash chromatography with methanol and dichloromethane as the eluant at a gradient of 0-10%
  7. additionThe fractions containing product
  8. customthe solvent was removed under reduced pressure

出典と根拠

ORDレコード
ord-b0c9da1282674b34911a58bd57e5586c
出典データセット
uspto-grants-2014_09
特許番号
US08822430B2

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