Morpholinosulfur trifluoride → N-tert-Butoxycarbonyl-(2R,4S)-4-fluoroproline benzyl ester

HRID 1244201ノート

反応式

HRID 1244201 の反応式
O1CCN(S(F)(F)[F:8])CC1.[N:11]1([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:26][C@H:24](O)[CH2:23][C@H:12]1[C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14]>C(Cl)Cl.O>[CH2:16]([O:15][C:13](=[O:14])[C@H:12]1[CH2:23][C@H:24]([F:8])[CH2:26][N:11]1[C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

参加物

5

反応物 2

HCID 2733258Morpholinosulfur trifluorideHCID 11902907Boc-hyp-obzl

生成物 1

HCID 69621870N-tert-Butoxycarbonyl-(2R,4S)-4-fluoroproline benzyl ester収率 48%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

Morpholinosulfur trifluoride (morph-DAST; 3.5 mL, 29 mmol) was added by syringe to a solution of 1 (6.5 g, 20 mmol) in dry CH2Cl2 (200 mL) under Ar(g) at −78° C. The solution w allowed to warm to room temperature and stirred overnight. Following a quench with methanol, the reaction mixture was washed with 2×100 mL saturated NaHCO3(aq). An emulsion resulted, so the mixture was diluted with H2O and CH2Cl2 and filtered through Celite. The biphasic filtrate was separated, and the organic layer was washed with water, dried over MgSO4(s), and concentrated by rotary evaporation under reduced pressure. The resulting oil was purified by flash chromatography (1.5% v/v MeOH in CH2Cl2), which afforded 11 (3.1 g, 9.6 mmol, 48%) as a yellow oil. An additional 2.32 g of 11 that were contaminated with a minor impurity, as indicated by TLC, were also obtained from the column.

後処理

  1. customa quench with methanol
  2. washthe reaction mixture was washed with 2×100 mL saturated NaHCO3(aq)
  3. customAn emulsion resulted
  4. filtrationfiltered through Celite
  5. customThe biphasic filtrate was separated
  6. washthe organic layer was washed with water
  7. dry with materialdried over MgSO4(s)
  8. concentrationconcentrated by rotary evaporation under reduced pressure
  9. customThe resulting oil was purified by flash chromatography (1.5% v/v MeOH in CH2Cl2), which

出典と根拠

ORDレコード
ord-0a0172a5c9174e088f02618fb562cbfa
出典データセット
uspto-grants-2006_10
特許番号
US07122521B2

反応ノート

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