Allyl bromide → Methyl 3-Allyl-1-Boc-pyrrolidine-3-carboxylate

HRID 1038026

反応式

HRID 1038026 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

HCID 11536331Methyl 3-Allyl-1-Boc-pyrrolidine-3-carboxylate収率 66.8%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-1e1ad64b3db84fb9a58cfdcf18df9aea
出典データセット
uspto-grants-2013_10
特許番号
US08546404B2

関連ノート

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