Benzyl Bromide → HCID 18782009, compound

HRID 1420538Notes

Reaction equation

HRID 1420538 reaction equation
[CH3:1][S:2][CH:3]1[NH:6][C:5](=[O:7])[CH2:4]1.[H-].[Na+].[CH2:10](Br)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C1COCC1>[CH3:1][S:2][CH:3]1[N:6]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:5](=[O:7])[CH2:4]1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 126772484-(Methylsulfanyl)azetidin-2-one

Product 1

HCID 18782009HCID 18782009, compoundYield 55.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of 4-methylthioazetidin-2-one (1.0 g, 8.53 mmol) in dry THF (10 ml) was added dropwise to a suspension of NaH (0.35 g, 8.63 mmol) in dry THF (5 ml) at -20° C. under an inert atmosphere. Benzyl bromide (1.46 g, 8.53 mmol) in dry THF (10 ml) was added dropwise over 15 minutes at -55° C. The resultant mixture was stirred for 2 hours at room temperature, poured onto ice/water (50 g) and filtered, washed with brine and water, dried (MgSO4), and evaporated under reduced pressure to a yellow oil (1.62 g). This was purified by flash chromatography on silica gel eluted with petroleum ether/ethyl acetate to give a yellow solid (0.98 g, 55%), m.p. 26-28° C.

Workup

  1. additionpoured onto ice/water (50 g)
  2. filtrationfiltered
  3. washwashed with brine and water
  4. dry with materialdried (MgSO4)
  5. customevaporated under reduced pressure to a yellow oil (1.62 g)
  6. customThis was purified by flash chromatography on silica gel
  7. washeluted with petroleum ether/ethyl acetate

Sources & evidence

ORD record
ord-ab42f6f61b5447e38a7da9c9fcacd801
Source dataset
uspto-grants-2000_06
Patent number
US06071899

Reaction notes

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