Sodium Hydroxide → (S)-2-(1-BOC-2-pyrrolidinyl)acetic acid

HRID 458476

반응식

HRID 458476 반응식
C[O:2][C:3](=[O:17])[CH2:4][C@@H:5]1[CH2:9][CH2:8][CH2:7][N:6]1[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11].[OH-].[Na+]>CO>[C:13]([O:12][C:10]([N:6]1[CH2:7][CH2:8][CH2:9][C@H:5]1[CH2:4][C:3]([OH:17])=[O:2])=[O:11])([CH3:16])([CH3:14])[CH3:15]

참가 물질

4

반응물 2

HCID 14798Sodium HydroxideHCID 11075654METHYL (2S)-PYRROLIDIN-2-YLACETATE

생성물 1

HCID 688605(S)-2-(1-BOC-2-pyrrolidinyl)acetic acid수율 92.6%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

tert-Butyl (2S)-2-(2-methoxy-2-oxoethyl)-1-pyrrolidinecarboxylate (8.35 g, 34.3 mmol) was dissolved in 150 mL MeOH. Aqueous NaOH (50 mL, 1 M) was added and the reaction mixture was allowed to stand overnight. After concentration in vacuo to ca. 100 mL, the solution was added to 300 mL water and extracted with ether (2×). The carboxylate solution was acidified to pH 2 with 12 N HCl and extracted with ether (2×). The aqueous layer was saturated with salt and extracted a third time with ether. The combined organic layers were washed with water, brine and dried over MgSO4. Filtration and concentration provided the title acid as a white solid (7.28 g, 31.7 mmol, 92.6%): 1H NMR (300 MHz, CDCl3, mixture of rotamers) δ 4.16 (bs, 1H), 3.37 (bs, 2H), 3.0–2.8 (bs, 1H), 2.36 (dd, J=9.3, 15.3 Hz, 1H), 2.2–2.0 (m, 1H), 1.9–1.7 (m, 4H), 1.48 (s, 9H) ppm.

후처리

  1. concentrationAfter concentration in vacuo to ca. 100 mL
  2. additionthe solution was added to 300 mL water
  3. extractionextracted with ether (2×)
  4. extractionextracted with ether (2×)
  5. extractionextracted a third time with ether
  6. washThe combined organic layers were washed with water, brine
  7. dry with materialdried over MgSO4
  8. filtrationFiltration and concentration

출처 및 근거

ORD 기록
ord-105dda33601e4642bccaad5f98c8e52b
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07189851B2

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