Benzyl Bromide → HCID 18686046, compound

HRID 1357972Notes

Reaction equation

HRID 1357972 reaction equation
[OH:1][CH2:2][C@@H:3]1[C@H:7]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[CH:9]=2)[CH2:6][C:5](=[CH2:15])[CH2:4]1.[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[H-].[Na+]>CN(C=O)C.CCOCC>[CH2:16]([O:1][CH2:2][C@@H:3]1[C@H:7]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[CH:9]=2)[CH2:6][C:5](=[CH2:15])[CH2:4]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 18686049HCID 18686049, compound

Product 1

HCID 18686046HCID 18686046, compoundYield 47.4%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-(S)-(hydroxymethyl)-4-(R)-(3-fluorophenyl)-1-methylenecyclopentane (3.11 g, 16.5 mmol) from Example 65, Step C in DMF (100 mL) was added benzyl bromide (4.24 g, 24.8 mmol) and then sodium hydride (60% in mineral oil, 0.73 g, 18.2 mmol) portionwise over 5 min. The reaction was stirred at rt for 16 h, then diluted with ether (100 mL) and quenched slowly into aq. sodium bicarbonate (200 mL). The layers were separated and the aqueous was extracted with ether. The organic layers were washed 3× with water, then brine, dried over sodium sulfate and concentrated. The residue (7 g) was purified by FC using 0.5-1% ethyl acetate in hexanes to afford the title compound (2.32 g).

Workup

  1. customquenched slowly into aq. sodium bicarbonate (200 mL)
  2. customThe layers were separated
  3. extractionthe aqueous was extracted with ether
  4. washThe organic layers were washed 3× with water
  5. dry with materialbrine, dried over sodium sulfate
  6. concentrationconcentrated
  7. customThe residue (7 g) was purified by FC

Sources & evidence

ORD record
ord-62ce84a450c54be3a3ba5a98058cbd83
Source dataset
uspto-grants-2003_07
Patent number
US06593346B2

Reaction notes

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