Benzyl Bromide → HCID 178500717, compound

HRID 2092000Notes

Reaction equation

HRID 2092000 reaction equation
[CH3:1][O:2][C:3](=[O:10])[CH2:4][C@H:5]1[CH2:8][C@H:7]([OH:9])[CH2:6]1.[H-].[Na+].[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CN(C=O)C>[CH3:1][O:2][C:3](=[O:10])[CH2:4][C@H:5]1[CH2:8][C@H:7]([O:9][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:6]1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 178500716HCID 178500716, compound

Product 1

HCID 178500717HCID 178500717, compoundYield 40.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution trans-(3-hydroxy-cyclobutyl)-acetic acid methyl ester (168 mg, 1.17 mmol) in DMF (1.5 mL) is added, NaH (60% in oil, 70 mg, 1.75 mmol) at 0° C. After stirring at 0° C. for 15 minutes, benzyl bromide (167 uL, 1.40 mmol) is added at 0° C. The mixture is stirred at room temperature for 2 hours and quenched with H2O. The mixture is extracted with dichloromethane, and the organic layer is concentrated under reduced pressure. The obtained residue is purified by silica gel column chromatography to give trans-(3-benzyloxy-cyclobutyl)-acetic acid methyl ester (110 mg, 40%); ESI-MS m/z 235 [M+1]+, retention time 1.97 min (condition A).

Workup

  1. customat 0° C
  2. stirringThe mixture is stirred at room temperature for 2 hours
  3. customquenched with H2O
  4. extractionThe mixture is extracted with dichloromethane
  5. concentrationthe organic layer is concentrated under reduced pressure
  6. customThe obtained residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-8566bf2b65f14f00a1ce960c55523072
Source dataset
uspto-grants-2013_05
Patent number
US08440682B2

Reaction notes

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