2,6-Lutidine → HCID 86727023, compound

HRID 1472226Notes

Reaction equation

[C:1]([O:5][C:6](=[O:19])[CH2:7][CH:8]([OH:18])[CH2:9][O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([CH3:4])([CH3:3])[CH3:2].N1C(C)=CC=CC=1C.[Si:28](OS(C(F)(F)F)(=O)=O)([C:31]([CH3:34])([CH3:33])[CH3:32])([CH3:30])[CH3:29]>C(Cl)Cl.CCOC(C)=O>[CH2:11]([O:10][CH2:9][CH:8]([O:18][Si:28]([C:31]([CH3:34])([CH3:33])[CH3:32])([CH3:30])[CH3:29])[CH2:7][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:19])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of tert-butyl-4-(benzyloxy)-3-hydroxybutanoate XXXV [Tetrahedron (1993), 49(10), 1997-2010] (2.3 g, 8.84 mmol) in DCM (100 mL) at 0° C. was added 2,6-lutidine (3.07 mL, 26.52 mmol) and TBSOTf (4 mL, 4. 17.68 mmol). After stirring for 16 h at 0° C., the reaction was diluted with EtOAc (400 mL). The mixture was washed with 1N HCl, saturated aq NaHCO3, water and dried. The extract was dried (MgSO4) and concentrated under reduced pressure. Purification of the crude product by column chromatography (100% hexane→25% EtOAc/hexane) afforded tert-butyl 4-(benzyloxy)-3-(tert-butyldimethylsilyloxy)butanoate XXXVI (3.1 g, 8.15 mmol, 92.1% yield) as a colorless oil.

Workup

washThe mixture was washed with 1N HCl, saturated aq NaHCO3, water
customdried
dry with materialThe extract was dried (MgSO4)
concentrationconcentrated under reduced pressure
customPurification of the crude product by column chromatography (100% hexane→25% EtOAc/hexane)

Sources & evidence

ORD record: ord-5df00271881b40cebc7c7e199a97ddc9
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09012491B2

Reaction notes

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