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

HRID 1968875ノート

反応式

HRID 1968875 の反応式
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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
-65 °C

実験手順

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].

後処理

  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

出典と根拠

ORDレコード
ord-1d7bfe9c73174aaabb4bedb2747d1029
出典データセット
uspto-grants-2013_04
特許番号
US08426414B2

反応ノート

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