Diethyl Ether → HCID 67959083, compound

HRID 1404960Notes

Reaction equation

HRID 1404960 reaction equation
Br[C:2]1[C:11]2[O:10][CH2:9][CH2:8][N:7](C(OC(C)(C)C)=O)[CH2:6][C:5]=2[S:4][CH:3]=1.CCOCC.C([Li])CCC.[C:29]1(=[O:33])[CH2:32][CH2:31][CH2:30]1>O.CCCCCC>[O:10]1[C:11]2[C:2]([C:29]3([OH:33])[CH2:32][CH2:31][CH2:30]3)=[CH:3][S:4][C:5]=2[CH2:6][NH:7][CH2:8][CH2:9]1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 14496CyclobutanoneHCID 67959348HCID 67959348, compoundHCID 178418339Butyllithium

Product 1

HCID 67959083HCID 67959083, compoundYield 58.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8058HexaneSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of tert-butyl 8-bromo-2,3-dihydrothieno[2,3-f][1,4]oxazepine-4(5H)-carboxylate (334 mg) obtained in Example 1, steps 1-3, and Et2O (10 mL) was added dropwise 1.6 N hexane solution of n-butyllithium (72.4 ml) at −78° C., and the mixture was stirred at −78° C. for 15 min. Cyclobutanone (0.0747 ml) was added, and the mixture was stirred at −78° C. for 1 hr. To the reaction mixture was added water (10 mL), and the organic layer was separated and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (solvent gradient; 0→50% ethyl acetate/hexane) to give the title compound (190 mg, 58.5%) as an oil.

Workup

  1. stirringthe mixture was stirred at −78° C. for 1 hr
  2. customthe organic layer was separated
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (solvent gradient; 0→50% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-c17957dc14ba45e7a39d29fb35a93c9c
Source dataset
uspto-grants-2014_12
Patent number
US08916549B2

Reaction notes

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