Sodium Hydroxide → 1-((Tert-butoxy)carbonyl)-3-methylpyrrolidine-3-carboxylic acid

HRID 1922644ノート

反応式

HRID 1922644 の反応式
C[O:2][C:3]([C:5]1([CH3:17])[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6]1)=[O:4].[OH-].[Na+]>>[C:13]([O:12][C:10]([N:7]1[CH2:8][CH2:9][C:5]([CH3:17])([C:3]([OH:4])=[O:2])[CH2:6]1)=[O:11])([CH3:16])([CH3:14])[CH3:15]

参加物

3

反応物 2

HCID 14798Sodium HydroxideHCID 113340041-Tert-butyl 3-methyl 3-methylpyrrolidine-1,3-dicarboxylate

生成物 1

HCID 532554551-((Tert-butoxy)carbonyl)-3-methylpyrrolidine-3-carboxylic acid収率 100%

実験手順

To a solution of 3-methylpyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-methyl ester (370 mg, 1.52 mmol) in IMS (5 mL) was added a 1M aqueous solution of sodium hydroxide (2.0 mL, 2.0 mmol). The reaction mixture was stirred at room temperature for 2 hours, and then concentrated under reduced pressure. The residue was partitioned between EtOAc and a 0.1M aqueous solution of HCl. The organic layer was separated and washed with brine, dried over Na2SO4, filtered and concentrated to give the desired product as a white solid (348 mg, 100%). 1H NMR (400 MHz, CHCl3-d): 6 3.85-3.75 (m, 1H); 3.52-3.41 (m, 2H); 3.27-3.15 (m, 1H); 2.39-2.30 (m, 1H); 1.83-1.74 (m, 1H); 1.51-1.40 (m, 9H); 1.38 (s, 3H).

後処理

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was partitioned between EtOAc
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-6c0749d86cec401dac88609949e26e06
出典データセット
uspto-grants-2012_05
特許番号
US08173650B2

反応ノート

読み込み中…