Methyl iodide → N-BOC-2-methyl-4-(S)-phenyl-(L)-proline, methyl ester

HRID 496234ノート

反応式

HRID 496234 の反応式
[C:1]([N:8]1[CH2:16][C@H:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:14][C@H:9]1[C:10]([O:12][CH3:13])=[O:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[Li+].[CH3:24][Si]([N-][Si](C)(C)C)(C)C.CI>C1COCC1>[C:1]([N:8]1[CH2:16][C@H:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:14][C@@:9]1([CH3:24])[C:10]([O:12][CH3:13])=[O:11])([O:3][C:4]([CH3:6])([CH3:7])[CH3:5])=[O:2]

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 2733832Lithium HexamethyldisilazideHCID 580029141-(tert-Butyl) 2-methyl (2S,4S)-4-phenylpyrrolidine-1,2-dicarboxylate

生成物 1

HCID 131725143N-BOC-2-methyl-4-(S)-phenyl-(L)-proline, methyl ester

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

To a solution of N-BOC-4-(S)-phenyl-(L)-proline, methyl ester from Step A (2.0 g, 6.56 mmol) in anhydrous THF (20 mL) at −78° C. was added over a 30 min period 1M LiHMDS in hexanes (9.83 mL, 9.83 mmol) and allowed to stir for 30 mins at −78° C. The reaction was then allowed to stir for 1 hr at 0° C. The reaction was then cooled to −78° C. and MeI (4.65 g, 32.79 mmol) was added dropwise. The reaction was allowed to warm to rt overnight. The reaction was quenched with NH4Cl. The organic layer was collected and washed with 1M HCl, NaHCO3, brine, dried over anhydrous MgSO4 and concentrated in vacuo. The crude product was purified by flash column chromatography on silica gel eluted with 75% Et2O/hexanes to give 1.85 g of desired product.

後処理

  1. stirringto stir for 1 hr at 0° C
  2. temperatureThe reaction was then cooled to −78° C.
  3. temperatureto warm to rt overnight
  4. customThe reaction was quenched with NH4Cl
  5. customThe organic layer was collected
  6. washwashed with 1M HCl, NaHCO3, brine
  7. dry with materialdried over anhydrous MgSO4
  8. concentrationconcentrated in vacuo
  9. customThe crude product was purified by flash column chromatography on silica gel
  10. washeluted with 75% Et2O/hexanes

出典と根拠

ORDレコード
ord-f889c88ca0774d68bcbae257962622fd
出典データセット
uspto-grants-2005_09
特許番号
US06943180B2

反応ノート

読み込み中…