Dimethyl Sulfoxide → (4-Formyltetrahydropyran-4-yl)carbamic acid tert-butyl ester

HRID 1968875노트

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HRID 1968875 반응식
CS(C)=O.C(Cl)(=O)C(Cl)=O.[C:11]([O:15][C:16](=[O:26])[NH:17][C:18]1([CH2:24][OH:25])[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1)([CH3:14])([CH3:13])[CH3:12].C(N(CC)CC)C>ClCCl>[C:11]([O:15][C:16](=[O:26])[NH:17][C:18]1([CH:24]=[O:25])[CH2:19][CH2:20][O:21][CH2:22][CH2:23]1)([CH3:14])([CH3:12])[CH3:13]

참가 물질

6

반응물 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 67114425tert-butyl N-[4-(hydroxymethyl)oxan-4-yl]carbamate

생성물 1

HCID 59718793(4-Formyltetrahydropyran-4-yl)carbamic acid tert-butyl ester수율 92.6%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

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온도
-65 °C

실험 절차

Anhydrous dimethyl sulfoxide (3.0 mL, 42.2 mmol) was added to a −65° C. solution of oxalyl chloride (2.0 mL, 22.9 mmol) in anhydrous dichloromethane (100 mL) and allowed to stir at −65° C. under N2 blanket for 3 minutes, after which time a solution of (4-hydroxymethyl-tetrahydro-pyran-4-yl)-carbamic acid tert-butyl ester (4.89 g, 21.1 mmol) in anhydrous dichloromethane (25 mL) was added. When 25 minutes had elapsed, triethylamine (14.7 mL, 105.5 mmol) was added and the reaction solution allowed to stir for a further 20 minutes at −65° C.; then the cold bath was removed and the reaction warmed to ambient temperature, washed with saturated aqueous sodium chloride (500 mL), dried (MgSO4), and evaporated to afford 4.48 g of clear yellow viscous liquid which was used without further purification. LRMS (ESI) m/z 230.2 [(M+H)+, calcd for C11H20NO4230.3].

후처리

  1. customWhen 25 minutes
  2. stirringto stir for a further 20 minutes at −65° C.
  3. customthen the cold bath was removed
  4. temperaturethe reaction warmed to ambient temperature
  5. washwashed with saturated aqueous sodium chloride (500 mL)
  6. dry with materialdried (MgSO4)
  7. customevaporated

출처 및 근거

ORD 기록
ord-1d7bfe9c73174aaabb4bedb2747d1029
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08426414B2

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