Triethylamine → (3R)-3-hydroxy-1-(p-nitrobenzyloxycarbonyl)pyrrolidine

HRID 891718노트

반응식

HRID 891718 반응식
Cl.[OH:2][C@@H:3]1[CH2:7][CH2:6][NH:5][CH2:4]1.[N+:8]([C:11]1[CH:21]=[CH:20][C:14]([CH2:15][O:16][C:17](Cl)=[O:18])=[CH:13][CH:12]=1)([O-:10])=[O:9].C(N(CC)CC)C>C(Cl)Cl>[OH:2][C@@H:3]1[CH2:7][CH2:6][N:5]([C:17]([O:16][CH2:15][C:14]2[CH:13]=[CH:12][C:11]([N+:8]([O-:10])=[O:9])=[CH:21][CH:20]=2)=[O:18])[CH2:4]1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 782054-Nitrobenzyl chloroformateHCID 2759336(3R)-pyrrolidin-3-ol hydrochloride

생성물 1

HCID 69544008(3R)-3-hydroxy-1-(p-nitrobenzyloxycarbonyl)pyrrolidine수율 90.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a suspension of (3R)-3-hydroxypyrrolidine hydrochloride (7.00 g, 56.6 mmol) in methylene chloride (210 ml) were added chloroformic acid p-nitrobenzyl ester (13.4 g, 62.3 mmol) and triethylamine (17.4 ml, 125 mmol) in an ice bath. The mixture was stirred at room temperature for 5 hours. After checking the completion of the reaction, the reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium hydrogencarbonate solution. The obtained organic layer was washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column using n-hexane:ethyl acetate (1:1)→ethyl acetate as the eluant to afford (3R)-3-hydroxy-1-(p-nitrobenzyloxycarbonyl)-pyrrolidine (13.6 g, yield 90%) as a pale yellow solid.

후처리

  1. customthe completion of the reaction
  2. customthe reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium hydrogencarbonate solution
  3. washThe obtained organic layer was washed with saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by chromatography on a silica gel column

출처 및 근거

ORD 기록
ord-013915be61174470b438ae8abf60afdb
출처 데이터셋
uspto-grants-2006_02
특허 번호
US07001897B2

반응 노트

불러오는 중…