Ammonium Chloride → Tert-butyl 3-benzoylpyrrolidine-1-carboxylate

HRID 253548

반응식

HRID 253548 반응식
CON(C)[C:4]([CH:6]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7]1)=[O:5].[C:19]1([Mg]Br)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[NH4+].[Cl-]>C1COCC1>[C:4]([CH:6]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:15])([CH3:16])[CH3:17])=[O:12])[CH2:7]1)(=[O:5])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

참가 물질

5

반응물 3

HCID 25517Ammonium ChlorideHCID 57419605Tert-butyl 3-[methoxy(methyl)carbamoyl]pyrrolidine-1-carboxylateHCID 178418255HCID 178418255, 화합물

생성물 1

HCID 57419606Tert-butyl 3-benzoylpyrrolidine-1-carboxylate수율 84%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

A stirred solution of tert-butyl 3-(methoxy(methyl)carbamoyl)pyrrolidine-1-carboxylate (2.27 g, 8.8 mmol) in dry THF (40 mL) was cooled in an ice bath and 1 M PhMgBr in THF (20 mL, 20.0 mmol) was added dropwise over 2 min. The mixture was stirred and the ice bath was allowed to melt. After 3 h, the mixture was poured into satd aq NH4Cl and extracted with ether (2×200 mL). The combined ether extracts were dried over MgSO4 and concentrated to leave an oil. Flash chromatography on a 40-g silica cartridge eluted with a 0 to 50% EtOAc in hexanes gradient afforded tert-butyl 3-benzoylpyrrolidine-1-carboxylate (2.04 g, 84%) as a clear colorless oil.

후처리

  1. extractionextracted with ether (2×200 mL)
  2. dry with materialThe combined ether extracts were dried over MgSO4
  3. concentrationconcentrated
  4. customto leave an oil
  5. washFlash chromatography on a 40-g silica cartridge eluted with a 0 to 50% EtOAc in hexanes gradient

출처 및 근거

ORD 기록
ord-5d615d594bd84870829e90a9238e3944
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07872028B2

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