Dicyclohexylcarbodiimide → (R)-quinuclidin-3-yl 2-(2-oxopyrrolidin-1-yl)-2-phenylacetate

HRID 404666노트

반응식

HRID 404666 반응식
[O:1]=[C:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH:7]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:8]([OH:10])=[O:9].C1CCC(N=C=NC2CCCCC2)CC1.C1C=CC2N(O)N=NC=2C=1.[N:42]12[CH2:49][CH2:48][CH:45]([CH2:46][CH2:47]1)[C@@H:44](O)[CH2:43]2>C1COCC1>[O:1]=[C:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH:7]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:8]([O:10][C@@H:44]1[CH:45]2[CH2:48][CH2:49][N:42]([CH2:47][CH2:46]2)[CH2:43]1)=[O:9]

참가 물질

6

반응물 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 914043-Quinuclidinol, (-)-HCID 132542962-(2-Oxopyrrolidin-1-yl)-2-phenylacetic acid

생성물 1

HCID 86688927(R)-quinuclidin-3-yl 2-(2-oxopyrrolidin-1-yl)-2-phenylacetate수율 93.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A mixture of 2-(2-oxopyrrolidin-1-yl)-2-phenylacetic acid (345 mg, 1.57 mmol), DCC (649 mg, 3.15 mmol), HOBT (425 mg, 3.15 mmol) and (R)-quinuclidin-3-ol (400 mg, 3.15 mmol) in dry THF (15.7 ml) was stirred at room temperature for 24 hours. The yellow suspension was filtered washing the white solid with THF. The yellow solution was evaporated and the crude was purified by flash chromatography (DCM/MeOH=96/4+0.4% NH4OH) to collect the title compound (482 mg, 93% yield) as a pale yellow oil.

후처리

  1. filtrationThe yellow suspension was filtered
  2. washwashing the white solid with THF
  3. customThe yellow solution was evaporated
  4. customthe crude was purified by flash chromatography (DCM/MeOH=96/4+0.4% NH4OH)

출처 및 근거

ORD 기록
ord-55d106f6108d44d5991f84052298f4e2
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08748613B2

반응 노트

불러오는 중…