Sodium Bicarbonate → HCID 67312716, 화합물

HRID 1010912노트

반응식

HRID 1010912 반응식
[CH2:1]([O:8][C:9]([N:11]1[CH2:18][CH2:17][CH2:16][C@@:12]1([CH3:19])[C:13](O)=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])O.[Na+]>O1CCCC1>[OH:14][CH2:13][C@:12]1([CH3:19])[CH2:16][CH2:17][CH2:18][N:11]1[C:9]([O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:10]

참가 물질

4

반응물 2

HCID 516892Sodium BicarbonateHCID 18604408HCID 18604408, 화합물

생성물 1

HCID 67312716HCID 67312716, 화합물수율 62.6%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a solution obtained by dissolving 840 mg of the compound [63-1] in 16 mL of tetrahydrofuran, 4.31 mL of a borane-methyl sulfide complex (a 2 M tetrahydrofuran solution) was added at room temperature, and the mixture was heated under reflux for 4 hours. To the reaction solution, a saturated aqueous sodium hydrogen carbonate solution was added, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The insolubles were filtered, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=100/0 to 60/40) to obtain 498 mg of benzyl (2S)-2-(hydroxymethyl)-2-methylpyrrolidine-1-carboxylate [63-2] (hereinafter, referred to as the compound [63-2]).

후처리

  1. customTo a solution obtained
  2. additionwas added at room temperature
  3. temperaturethe mixture was heated
  4. temperatureunder reflux for 4 hours
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe obtained organic layer was washed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationThe insolubles were filtered
  9. concentrationthe filtrate was concentrated under reduced pressure
  10. customThe obtained residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=100/0 to 60/40)

출처 및 근거

ORD 기록
ord-73b011ab4834440a968cb7c9d56dfd28
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07977336B2

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