Ethyl Acetate → benzyl (2S,3S)-3-hydroxy-2,3-dimethylpyrrolidine-1-carboxylate

HRID 1173585노트

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HRID 1173585 반응식
[Cl-].[Ce+3].[Cl-].[Cl-].C[Mg]Br.[CH2:8](OCC)C.[CH3:13][C@H:14]1[C:18](=[O:19])[CH2:17][CH2:16][N:15]1[C:20]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:21].C(OCC)(=O)C>C1COCC1>[OH:19][C@@:18]1([CH3:8])[CH2:17][CH2:16][N:15]([C:20]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:21])[C@H:14]1[CH3:13]

참가 물질

6

반응물 4

HCID 8857Ethyl AcetateHCID 24636Cerium(III) chlorideHCID 59556933benzyl (2S)-2-methyl-3-oxopyrrolidine-1-carboxylateHCID 178467822HCID 178467822, 화합물

생성물 1

HCID 59557026benzyl (2S,3S)-3-hydroxy-2,3-dimethylpyrrolidine-1-carboxylate수율 84%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
-78 °C

실험 절차

A suspension of cerium chloride (47 g) in THF (300 mL) was cooled to −78° C., methylmagnesium bromide-diethyl ether solution (56 mL, 3 mol/L) was added dropwise while adjusting the solution temperature to −70° C. or below. After the completion of the dropwise addition, the mixture was stirred at −78° C. for 30 min, a solution of benzyl(2S)-2-methyl-3-oxopyrrolidine-1-carboxylate (18 g) in THF (60 mL) was added dropwise while adjusting the solution temperature to −70° C. or below. The reaction mixture was warmed to 0° C. over 2 hr, ethyl acetate (1 L) was added, and insoluble materials were filtered off. The filtrate was partitioned with water, and the organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=9/1→1/1) to give the title compound as a colorless oil (yield: 16.2 g, 84%).

후처리

  1. customto −70° C. or below
  2. additionAfter the completion of the dropwise addition
  3. customto −70° C. or below
  4. temperatureThe reaction mixture was warmed to 0° C. over 2 hr
  5. filtrationinsoluble materials were filtered off
  6. customThe filtrate was partitioned with water
  7. washthe organic layer was washed with saturated brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=9/1→1/1)

출처 및 근거

ORD 기록
ord-0b32a61df77c47d9915374284832dad3
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07834051B2

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