Triacetoxyperiodinane → tert-Butyl-(2S,3R)-3-{[tert-butyl(dimethyl)silyl]oxy}-2-formylpyrrolidine-1-carboxylate

HRID 751107

반응식

HRID 751107 반응식
[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]

참가 물질

4

반응물 2

HCID 159087TriacetoxyperiodinaneHCID 11012982(2R,3R)-3-(tert-Butyldimethylsilanyloxy)-2-hydroxymethylpyrrolidine-1-carboxylic acid tert-butyl ester

생성물 1

HCID 16732142tert-Butyl-(2S,3R)-3-{[tert-butyl(dimethyl)silyl]oxy}-2-formylpyrrolidine-1-carboxylate수율 108%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To (2R,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester (51B) (6.70 g, 20.24 mmol) in CH2Cl2 (100 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, the organic layer was washed with a mixture of saturated aqueous Na2S2O3 and NaHCO3 followed by brine, dried (MgSO4), and was then filtered and concentrated to obtain the title compound (7.20 g) as a yellow oil.

후처리

  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 NaHCO3
  5. dry with materialdried (MgSO4)
  6. filtrationwas then filtered
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-773c7d7c1af44f4e933181c156d024fd
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07405234B2

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