Methanol → (R)-2-(4-Bromobenzyl)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid

HRID 2182615노트

반응식

HRID 2182615 반응식
C([O:3][C:4](=[O:25])[C@:5]1([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([Br:24])=[CH:20][CH:19]=2)[CH2:9][CH2:8][CH2:7][N:6]1[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])C.[Li+].[OH-].C1COCC1.CO>O>[C:13]([O:12][C:10]([N:6]1[CH2:7][CH2:8][CH2:9][C@@:5]1([CH2:17][C:18]1[CH:23]=[CH:22][C:21]([Br:24])=[CH:20][CH:19]=1)[C:4]([OH:25])=[O:3])=[O:11])([CH3:16])([CH3:14])[CH3:15]

참가 물질

6

반응물 4

HCID 887MethanolHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 69212228N-(tert-butoxycarbonyl)-2-(4-bromobenzyl)proline ethyl ester

생성물 1

HCID 2761850(R)-2-(4-Bromobenzyl)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid수율 108%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

A mixture of N-(tert-butoxycarbonyl)-2-(4-bromobenzyl)proline ethyl ester (3.00 g), LiOH (10 mmol), THF (25 mL), MeOH (10 mL) and H2O (5 mL) was stirred at room temperature overnight. The mixture was then heated at 74° C. overnight. The mixture was concentrated in vacuo, and water was added. The mixture was washed with Et2O and the aqueous layer was made acidic with the addition of 1N H2SO4. The aqueous layer was extracted with EtOAc. The EtOAc layer was washed with brine, dried over Na2SO4, and evaporated to give N-(tert-butoxycarbonyl)-2-(4-bromobenzyl)proline (3.02 g). MS (m/z) 284 (MH+-t-Boc); mp: 143.9° C.

후처리

  1. temperatureThe mixture was then heated at 74° C. overnight
  2. concentrationThe mixture was concentrated in vacuo, and water
  3. additionwas added
  4. washThe mixture was washed with Et2O
  5. additionthe aqueous layer was made acidic with the addition of 1N H2SO4
  6. extractionThe aqueous layer was extracted with EtOAc
  7. washThe EtOAc layer was washed with brine
  8. dry with materialdried over Na2SO4
  9. customevaporated

출처 및 근거

ORD 기록
ord-76ba3c8e568549a2809cf05b71b54723
출처 데이터셋
uspto-grants-2005_05
특허 번호
US06897225B1

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