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

HRID 1968875Notes

Reaction equation

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]

Participants

Conditions

Temperature: -65 °C

Procedure

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].

Workup

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

Sources & evidence

ORD record: ord-1d7bfe9c73174aaabb4bedb2747d1029
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08426414B2

Reaction notes

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