Ammonium Chloride → 1-tert-butyl 2-methyl (2S)-4-methylidenepyrrolidine-1,2-dicarboxylate

HRID 457906ノート

反応式

HRID 457906 の反応式
[CH3:1]C(C)([O-])C.[K+].O=[C:8]1[CH2:12][N:11]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C@H:10]([C:20]([O:22][CH3:23])=[O:21])[CH2:9]1.[Cl-].[NH4+]>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(OCC)C>[CH2:1]=[C:8]1[CH2:12][N:11]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C@H:10]([C:20]([O:22][CH3:23])=[O:21])[CH2:9]1

参加物

6

反応物 3

HCID 25517Ammonium ChlorideHCID 109884851-tert-butyl 2-methyl (2S)-4-oxopyrrolidine-1,2-dicarboxylateHCID 23665647Potassium tert-butoxide

生成物 1

HCID 157359851-tert-butyl 2-methyl (2S)-4-methylidenepyrrolidine-1,2-dicarboxylate収率 70%

試薬・触媒・溶媒 2

HCID 74505Methyltriphenyliphosphonium bromide触媒HCID 3283Diethyl Ether溶媒

反応条件

温度
35 °C

実験手順

Methyltriphenylphosphonium bromide (22 g, 61.6 mmol) was added to a solution of potassium tert-butoxide (6.5 g, 57.6 mmol) in anhydrous diethyl ether (450 ml) at 0° C. under nitrogen and the resulting bright yellow mixture stirred for 30 minutes. A solution of 1-tert-butyl 2-methyl (2S)-4-oxo-1,2-pyrrolidinedicarboxylate (10 g, 41.1 mmol in 150 ml anhydrous diethyl ether) was added slowly to the reaction mixture, which was then warmed at 35° C. for 3 h. Saturated aqueous ammonium chloride solution (0.5 ml) was then added. The organic layer was removed, and the aqueous washed with diethyl ether (3×5 ml). The combined organic layers were dried with brine and magnesium sulfate before filtering and removal of solvent. Silica gel chromatography, eluting with 15% ethyl acetate in hexanes gave the desired product 6.9 g (70% yield) as a off-white wax.

後処理

  1. customThe organic layer was removed
  2. washthe aqueous washed with diethyl ether (3×5 ml)
  3. dry with materialThe combined organic layers were dried with brine and magnesium sulfate
  4. filtrationbefore filtering
  5. customremoval of solvent
  6. washSilica gel chromatography, eluting with 15% ethyl acetate in hexanes

出典と根拠

ORDレコード
ord-19c87251e75245ea9e9f5f7eeabef43b
出典データセット
uspto-grants-2007_03
特許番号
US07189754B2

反応ノート

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