Triacetoxyperiodinane → (2S,3S)-tert-Butyl 3-((tert-butyldimethylsilyl)oxy)-2-formylpyrrolidine-1-carboxylate

HRID 501640ノート

反応式

HRID 501640 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@H:10]([O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])[C@H:9]1[CH2:21][OH:22])=[O:7])([CH3:4])([CH3:3])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@H:10]([O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])[C@H:9]1[CH:21]=[O:22])=[O:7])([CH3:4])([CH3:3])[CH3:2]

参加物

4

反応物 2

HCID 159087TriacetoxyperiodinaneHCID 109256021,1-Dimethylethyl (2R,3S)-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-(hydroxymethyl)-1-pyrrolidinecarboxylate

生成物 1

HCID 16731848(2S,3S)-tert-Butyl 3-((tert-butyldimethylsilyl)oxy)-2-formylpyrrolidine-1-carboxylate収率 94.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To (2R,3S)-3-(tert-butyl-dimethylsilanyloxy)-2-hydroxymethyl pyrrolidine-1-carboxylic acid tert-butyl ester (61A) (9.85 g, 29.7 mmol) in CH2Cl2 (200 mL) at 0° C. was added Dess-Martin periodinane. The ice bath was removed and the reaction was warmed to rt. After 2 h, saturated aqueous Na2S2O3 and NaHCO3 (ca. 100 mL each) were added and the reaction mixture was stirred vigorously for 0.5 h. The layers were separated, and the organic layer was washed with a mixture of saturated aqueous Na2S2O3 and saturated aqueous NaHCO3 followed by brine, dried (MgSO4), and was then filtered and concentrated to obtain the title compound (9.23 g) as a yellow oil.

後処理

  1. customThe ice bath was removed
  2. additionsaturated aqueous Na2S2O3 and NaHCO3 (ca. 100 mL each) were added
  3. customThe layers were separated
  4. washthe organic layer was washed with a mixture of saturated aqueous Na2S2O3 and saturated aqueous NaHCO3
  5. dry with materialdried (MgSO4)
  6. filtrationwas then filtered
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-1cf5f9be02084d5c84dce388f54c2fc7
出典データセット
uspto-grants-2010_08
特許番号
US07772267B2

反応ノート

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