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

HRID 1749516ノート

反応式

HRID 1749516 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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]+.

後処理

  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)

出典と根拠

ORDレコード
ord-aacccbede0bc4938b40f76b78f9a125c
出典データセット
uspto-grants-2015_10
特許番号
US09156798B2

反応ノート

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