Butyl iodide → 2-Butyl-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

HRID 661512

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HRID 661512 반응식
[CH3:1][O:2][C:3]([CH:5]1[CH2:9][CH2:8][CH2:7][N:6]1[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[O:4].[Li+].C[Si]([N-][Si](C)(C)C)(C)C.I[CH2:28][CH2:29][CH2:30][CH3:31]>C1COCC1>[CH3:1][O:2][C:3]([C:5]1([CH2:28][CH2:29][CH2:30][CH3:31])[CH2:9][CH2:8][CH2:7][N:6]1[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[O:4]

참가 물질

5

반응물 3

HCID 10962Butyl iodideHCID 3941471-Tert-butyl 2-methyl pyrrolidine-1,2-dicarboxylateHCID 2733832Lithium Hexamethyldisilazide

생성물 1

HCID 666872182-Butyl-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester수율 69%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
-78 °C

실험 절차

To a stirred solution of pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (3.00 g, 13.1 mmol) in THF (50 mL) at −78° C. and under nitrogen was added LHMDS (14.4 mL of 1.0 M solution in THF, 14.4 mmol) dropwise. After 30 minutes, a solution of 1-iodobutane (2.23 mL, 19.7 mmol) in THF (1 mL) was added dropwise. The reaction mixture was stirred for 30 minutes at −78° C., warmed to ambient temperature over 90 minutes, then quenched by the addition of saturated aqueous NH4Cl and extracted with EtOAc. The combined extracts were washed with saturated aqueous NaHCO3 and brine then dried (MgSO4), filtered and concentrated in vacuo to a yellow oil (4.5 g). Purification by chromatography (silica, 10% EtOAc in hexanes) gave 2-butyl-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (2.57 g, 9.01 mmol, 69%) as a clear colourless oil.

후처리

  1. temperaturewarmed to ambient temperature over 90 minutes
  2. customquenched by the addition of saturated aqueous NH4Cl
  3. extractionextracted with EtOAc
  4. washThe combined extracts were washed with saturated aqueous NaHCO3 and brine
  5. dry with materialthen dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo to a yellow oil (4.5 g)
  8. customPurification by chromatography (silica, 10% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-eff591d2f427453ebf38d31f7e602612
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08084623B2

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