Triacetoxyperiodinane → tert-Butyl (6-oxospiro[3.3]heptan-2-yl)carbamate

HRID 1749516노트

반응식

HRID 1749516 반응식
[OH:1][CH:2]1[CH2:16][C:4]2([CH2:7][CH:6]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:5]2)[CH2:3]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[O:1]=[C:2]1[CH2:3][C:4]2([CH2:7][CH:6]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:12])([CH3:14])[CH3:13])[CH2:5]2)[CH2:16]1

참가 물질

5

반응물 3

HCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 253240582-(Boc-amino)-6-hydroxyspiro(3.3)heptane

생성물 1

HCID 39872257tert-Butyl (6-oxospiro[3.3]heptan-2-yl)carbamate수율 80.7%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of tert-butyl (6-hydroxyspiro[3.3]heptan-2-yl)carbamate (1.00 g, 4.40 mmol) in DCM (10 mL) was added Dess-Martin periodinane (2.80 g, 6.60 mmol) at ˜0° C. to 10° C. The resulting reaction mixture was stirred at room temperature for 1.5 h. The reaction mixture was treated with aqueous sodium bicarbonate and extracted with DCM. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate and filtered. Concentration under vacuum gave the crude product, which was purified by silica gel column chromatography (22% ethyl acetate in petroleum ether) to afford the title compound (800 mg, 3.55 mmol, 80% yield) as a pale yellow solid. MS (ESI) m/z 226.1 [M+H]+.

후처리

  1. customThe resulting reaction mixture
  2. extractionextracted with DCM
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationConcentration under vacuum
  7. customgave the crude product, which
  8. customwas purified by silica gel column chromatography (22% ethyl acetate in petroleum ether)

출처 및 근거

ORD 기록
ord-aacccbede0bc4938b40f76b78f9a125c
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09156798B2

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