N-Boc-4,4-difluoro-L-proline methyl ester → (2S)-1-[(tert-butoxy)carbonyl]-4,4-difluoropyrrolidine-2-carboxylic acid

HRID 525001

反応式

HRID 525001 の反応式
[F:1][C:2]1([F:18])[CH2:6][N:5]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[C@H:4]([C:14]([O:16]C)=[O:15])[CH2:3]1>CO.O1CCCC1.[OH-].[Na+]>[C:10]([O:9][C:7]([N:5]1[CH2:6][C:2]([F:1])([F:18])[CH2:3][C@H:4]1[C:14]([OH:16])=[O:15])=[O:8])([CH3:13])([CH3:11])[CH3:12]

参加物

5

反応物 1

HCID 11129200N-Boc-4,4-difluoro-L-proline methyl ester

生成物 1

HCID 22977458(2S)-1-[(tert-butoxy)carbonyl]-4,4-difluoropyrrolidine-2-carboxylic acid収率 99%

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒HCID 14798Sodium Hydroxide溶媒

実験手順

1.08 g (4.08 mmol) of (S)-1-tert-butyl 2-methyl 4,4-difluoropyrrolidine-1,2-dicarboxylate (purchased from Aldrich®; cat. no. 702463) were dissolved in a mixture of 10 mL of methanol and 10 mL of tetrahydrofurane and 6.12 mL of a 2M aqueous solution of sodium hydroxide were added. The solution was stirred at room temperature for 1 hour and then the organic solvents were removed. The remaining solution was diluted with water and 6.12 mL of 2M hydrochloric acid were added. The product that precipitated was extracted with dichloromethane (×3), the combined organic layers were washed with brine, dried over magnesium sulphate, filtered and the solvent was removed. 1.01 g (99% yield) of the title compound were obtained as a white solid.

後処理

  1. additionwere added
  2. customthe organic solvents were removed
  3. additionThe remaining solution was diluted with water and 6.12 mL of 2M hydrochloric acid
  4. additionwere added
  5. customThe product that precipitated
  6. extractionwas extracted with dichloromethane (×3)
  7. washthe combined organic layers were washed with brine
  8. dry with materialdried over magnesium sulphate
  9. filtrationfiltered
  10. customthe solvent was removed

出典と根拠

ORDレコード
ord-429dd18a78c443ad8a13d8876b6badf6
出典データセット
uspto-grants-2016_05
特許番号
US09340547B2

関連ノート

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