Triethylamine → Tert-butyl (3R)-3-(methanesulfonyloxy)pyrrolidine-1-carboxylate

HRID 472889

반응식

HRID 472889 반응식
[OH:1][C@@H:2]1[CH2:6][CH2:5][N:4]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:3]1.C(N(CC)CC)C.[CH3:21][S:22](Cl)(=[O:24])=[O:23]>C1(C)C=CC=CC=1>[CH3:21][S:22]([O:1][C@@H:2]1[CH2:6][CH2:5][N:4]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:3]1)(=[O:24])=[O:23]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 6544479tert-Butyl (3R)-3-hydroxypyrrolidine-1-carboxylate

생성물 1

HCID 10934372Tert-butyl (3R)-3-(methanesulfonyloxy)pyrrolidine-1-carboxylate수율 92%

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
-15 °C

실험 절차

To a solution of tert-butyl (R)-3-hydroxypyrrolidine-1-carboxylate (200 g, 1.07 mol) and triethylamine (167 g, 1.63 mol) in toluene (700 mL) at −20 to −30° C. was added methanesulfonyl chloride (156 g, 1.36 mol) drop-wise while maintaining the temperature at −10 to −20° C. The solution was warmed to ambient temperature and allowed to stir. The reaction solution was sampled hourly and analyzed by HPLC to establish completion of the reaction. Upon completion of the reaction, the suspension was filtered to remove the triethylamine hydrochloride. The filtrate was washed with ˜600 mL of dilute aqueous sodium bicarbonate solution. The organic layer was dried and concentrated under reduced pressure to give 2 as a viscous oil (260 g, 92%) which is used without further purification. 1H NMR (CDCl3, 400 MHz) δ 5.27 (m, 1H), 3.44-3.76 (m, 4H), 3.05 (s, 3H), 2.26 (m, 1H), 2.15 (m, 1H), 1.47 (s, 9H).

후처리

  1. temperatureThe solution was warmed to ambient temperature
  2. aliquotThe reaction solution was sampled hourly
  3. customcompletion of the reaction
  4. customUpon completion of the reaction
  5. filtrationthe suspension was filtered
  6. customto remove the triethylamine hydrochloride
  7. washThe filtrate was washed with ˜600 mL of dilute aqueous sodium bicarbonate solution
  8. customThe organic layer was dried
  9. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-d2f692192ac340f79708f4d4c671764b
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08633227B2

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