Allyl bromide → HCID 11536331, 화합물

HRID 1038026

반응식

HRID 1038026 반응식
[CH3:1][O:2][C:3]([CH:5]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6]1)=[O:4].[Li+].[CH3:18][CH:19]([N-]C(C)C)[CH3:20].C(Br)C=C>C1COCC1>[CH3:1][O:2][C:3]([C:5]1([CH2:20][CH:19]=[CH2:18])[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6]1)=[O:4]

참가 물질

5

반응물 3

HCID 7841Allyl bromideHCID 2724682Lithium diisopropylamideHCID 45727751-Tert-butyl 3-methyl pyrrolidine-1,3-dicarboxylate

생성물 1

HCID 11536331HCID 11536331, 화합물수율 66.8%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

Pyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-methyl ester 2 (see Example 1, Step 1) (4.58 g, 20 mmol) was dissolved in THF (100 mL) and cooled down to −78° C. in a dry ice-acetone bath. LDA (12 mL, 2.0 M, 24 mmol) was then added dropwise. The mixture was stirred at −78° C. for 1 hr. Allyl bromide (5.3 mL, 61 mmol) was added in neat. The reaction was allowed to warm to rt naturally and stirred for 24 hrs. It was then quenched with sat. NH4Cl solution, extracted with ethyl acetate 2×150 mL. The organic layer was washed with brine, dried (MgSO4) and concentrated. The crude was purified on silica gel column using 4:1 hexanes/ethyl acetate to get the title compound (3.6 g) as a yellow oil. MS (292, MNa).

후처리

  1. temperatureto warm to rt naturally
  2. stirringstirred for 24 hrs
  3. customIt was then quenched with sat. NH4Cl solution
  4. extractionextracted with ethyl acetate 2×150 mL
  5. washThe organic layer was washed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customThe crude was purified on silica gel column

출처 및 근거

ORD 기록
ord-1e1ad64b3db84fb9a58cfdcf18df9aea
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08546404B2

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