Carbon tetrabromide → Tert-butyl 3-(3,3-dibromoprop-2-en-1-yl)pyrrolidine-1-carboxylate

HRID 1253525노트

반응식

HRID 1253525 반응식
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]([Br:24])(Br)(Br)[Br:21].O=[CH:26][CH2:27][CH:28]1[CH2:32][CH2:31][N:30]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:29]1>ClCCl>[Br:21][C:20]([Br:24])=[CH:26][CH2:27][CH:28]1[CH2:32][CH2:31][N:30]([C:33]([O:35][C:36]([CH3:37])([CH3:39])[CH3:38])=[O:34])[CH2:29]1

참가 물질

5

반응물 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 53415273tert-Butyl 3-(2-oxoethyl)pyrrolidine-1-carboxylate

생성물 1

HCID 86657053Tert-butyl 3-(3,3-dibromoprop-2-en-1-yl)pyrrolidine-1-carboxylate

시약·촉매·용매 1

HCID 6344Dichloromethane용매3회

반응 조건

온도
0 °C

실험 절차

A flask was charged with triphenylphosphine (477 g, 1.82 mol) and dichloromethane (2,500 ml) was cooled to 0° C. A solution of carbon tetrabromide (302 g, 910 mmol) in dichloromethane (300 ml) was added dropwise, followed by the dropwise addition of a solution of tert-butyl 3-(2-oxoethyl)pyrrolidine-1-carboxylate (97 g, 455.40 mmol, 1.00 equiv) in dichloromethane (200 ml). The resulting solution was allowed stir for 1.5 hours at 0° C. The reaction mixture was washed with 4,000 ml of petroleum ether, and filtered. The filtrate was concentrated and the residue was purified by column chromatography on silica gel (ethyl acetate/petroleum ether gradient) to afford tert-butyl 3-(3,3-dibromoprop-2-en-1-yl)pyrrolidine-1-carboxylate as light yellow oil.

후처리

  1. washThe reaction mixture was washed with 4,000 ml of petroleum ether
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated
  4. customthe residue was purified by column chromatography on silica gel (ethyl acetate/petroleum ether gradient)

출처 및 근거

ORD 기록
ord-de9ba585e96e469a85df97ff22abb0ff
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08455477B2

반응 노트

불러오는 중…