Hydrochloric Acid → tert-Butyl 2-(hydroxymethyl)-1-oxo-8-azaspiro[4.5]decane-8-carboxylate

HRID 8753

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HRID 8753 반응식
[O:1]=[C:2]1[C:6]2([CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]2)[CH2:5][CH2:4][CH2:3]1.[CH:19](OCC)=[O:20].CC(C)([O-])C.[K+].Cl>C(OCC)C>[OH:20][CH2:19][CH:3]1[CH2:4][CH2:5][C:6]2([CH2:7][CH2:8][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:10][CH2:11]2)[C:2]1=[O:1]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 8025Ethyl formateHCID 10848487Tert-butyl 1-oxo-8-azaspiro(4.5)decane-8-carboxylateHCID 23665647Potassium tert-butoxide

생성물 1

HCID 21983946tert-Butyl 2-(hydroxymethyl)-1-oxo-8-azaspiro[4.5]decane-8-carboxylate수율 51.4%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

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온도
-78 °C

실험 절차

tert-Butyl 1-oxo-8-azaspiro[4.5]decane-8-carboxylate from Procedure 1, Step G (0.526 g, 2.08 mmol) was dried by evaporating with toluene (10 mL) three times in vacuo, dissolved in methyl-tert-butyl ether (5 mL), and cooled to −78° C. To this solution was added ethyl formate (0.336 mL, 4.15 mmol) and then potassium t-butoxide (0.466 g, 4.16 mmol). After 2 days, the reaction mixture was diluted with diethyl ether, poured into 2N HCl, and extracted three times with diethyl ether. The organic layers were combined, washed with brine, dried over sodium sulfate, filtered, and concentrated to afford 0.575 g. The residue was purified by flash chromatography eluting with 45% ethyl acetate/hexanes to give the title compound (0.303 g). MS/EI (acetonitrile/water): m/z 304 (M+1+Na) retention time=2.9 min.

후처리

  1. customby evaporating with toluene (10 mL) three times in vacuo
  2. dissolutiondissolved in methyl-tert-butyl ether (5 mL)
  3. extractionextracted three times with diethyl ether
  4. washwashed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto afford 0.575 g
  9. customThe residue was purified by flash chromatography
  10. washeluting with 45% ethyl acetate/hexanes

출처 및 근거

ORD 기록
ord-01aabc2e796f428ba758c5068521a6d6
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091211B2

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