Diisopropylethylamine → 3-(tert-Butyldimethylsilyloxy)cyclobutyl pivalate

HRID 1697219Notes

Reaction equation

HRID 1697219 reaction equation
[C:1]([O:7][CH:8]1[CH2:11][CH:10]([OH:12])[CH2:9]1)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].CCN(C(C)C)C(C)C.O([Si:30]([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31])S(C(F)(F)F)(=O)=O>C(Cl)Cl>[C:1]([O:7][CH:8]1[CH2:9][CH:10]([O:12][Si:30]([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31])[CH2:11]1)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 575158713-Hydroxycyclobutyl 2,2-dimethylpropanoate

Product 1

HCID 575158723-(tert-Butyldimethylsilyloxy)cyclobutyl pivalate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred mixture of 3-hydroxycyclobutyl pivalate (16.60 g, 96.4 mmol) and diea (25.2 ml, 145 mmol) in DCM (100 ml) at 0° C. was added tert-butyldimethylsilyl triflate (31.0 ml, 135 mmol) dropwise. The reaction was stirred for 2 h, then quenched with H2O. The layers were separated, and the organic layer was washed with saturated NaHCO3, brine, dried over MgSO4 and concentrated to give the title compound as a light brown oil.

Workup

  1. customquenched with H2O
  2. customThe layers were separated
  3. washthe organic layer was washed with saturated NaHCO3, brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-88e253786cff418d83412ce3fe5464c6
Source dataset
uspto-grants-2012_04
Patent number
US08163909B2

Reaction notes

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