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

HRID 1922644노트

반응식

HRID 1922644 반응식
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]

참가 물질

3

반응물 2

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

생성물 1

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

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-6c0749d86cec401dac88609949e26e06
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08173650B2

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