Benzyl Bromide → HCID 178500717, compound

HRID 217248Notes

Reaction equation

HRID 217248 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-7e35cc88492b4b118406cf317b84e25c
Source dataset
uspto-grants-2012_06
Patent number
US08193349B2

Reaction notes

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