2-Bromopropane → HCID 58292829, compound

HRID 1798089Notes

Reaction equation

HRID 1798089 reaction equation
[OH:1][B:2]1[C:6]2[CH:7]=[C:8]([O:12][CH:13]3[CH2:18][CH2:17][CH2:16][CH2:15][O:14]3)[CH:9]=[C:10]([OH:11])[C:5]=2[CH:4]([CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[O:3]1.C([O-])([O-])=O.[K+].[K+].Br[CH:32]([CH3:34])[CH3:33]>CN(C=O)C>[OH:1][B:2]1[C:6]2[CH:7]=[C:8]([O:12][CH:13]3[CH2:18][CH2:17][CH2:16][CH2:15][O:14]3)[CH:9]=[C:10]([O:11][CH:32]([CH3:34])[CH3:33])[C:5]=2[CH:4]([CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[O:3]1

Participants

5

Reactant 3

HCID 63582-BromopropaneHCID 11430Potassium CarbonateHCID 58292735HCID 58292735, compound

Product 1

HCID 58292829HCID 58292829, compoundYield 30.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of ethyl 2-(1,4-dihydroxy-6-(tetrahydro-2H-pyran-2-yloxy)-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate (320 mg, 0.95 mmol) and anhydrous K2CO3 (480 mg, 3.48 mmol) in DMF (10 mL) at 0° C. under N2 atmosphere was added 2-bromopropane (400 mg, 3.30 mmol). The reaction mixture was stirred at room temperature overnight and extracted with EtOAc (2×20 mL). The combined organic layers were dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by prep HPLC to give the title compound (110 mg. Yield: 30.6%)

Workup

  1. extractionextracted with EtOAc (2×20 mL)
  2. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by prep HPLC

Sources & evidence

ORD record
ord-ae8fd79838e041df82a7288b49e29883
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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