3-(1-Methylpyrrolidin-2-yl)pyridine → (R)-Nicotine

HRID 389169

반응식

HRID 389169 반응식
C([C@@](C(O)=O)(O)[C@@](C(=O)C1C=CC=CC=1)(O)C(O)=O)(=O)C1C=CC=CC=1.C(O)(C)C.[CH3:31][N:32]1[CH:36]([C:37]2[CH:42]=[CH:41][CH:40]=[N:39][CH:38]=2)[CH2:35][CH2:34][CH2:33]1>CO>[N:39]1[CH:38]=[C:37]([C@H:36]2[CH2:35][CH2:34][CH2:33][N:32]2[CH3:31])[CH:42]=[CH:41][CH:40]=1

참가 물질

5

반응물 3

HCID 9423-(1-Methylpyrrolidin-2-yl)pyridineHCID 3776IsopropanolHCID 12362976dibenzoyl-L(+)tartaric acid

생성물 1

HCID 157672(R)-Nicotine수율 57.6%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

A mixture of dibenzoyl-l-tartaric acid (58 g, 0.154 mol), 100 ml isopropanol and (R,S)-nicotine (25 g, 0.154 mol) was stirred for 1 hr and heated to reflux. While refluxing, 50 ml methanol was added and continued as in Example 1 to get (R)-nicotine (7.2 g, 57.6% yield) 99.85% GC, optical rotation: +141°, 99.9% chiral purity by HPLC.

후처리

  1. temperatureheated to reflux
  2. temperatureWhile refluxing

출처 및 근거

ORD 기록
ord-39b0e72307044c84870e7de79c6b53c9
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08378111B2

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