2-Methoxypropene → HCID 18341303, compound

HRID 382211Notes

Reaction equation

HRID 382211 reaction equation
[Br:1][CH2:2][C:3]([NH:5][C@H:6]([CH2:14][OH:15])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:4].O.[C:17]1(C)[CH:22]=CC(S(O)(=O)=O)=C[CH:18]=1.COC(C)=C>C(Cl)Cl>[Br:1][CH2:2][C:3]([N:5]1[C@@H:6]([CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:14][O:15][C:17]1([CH3:22])[CH3:18])=[O:4]

Participants

5

Reactant 3

HCID 83002-MethoxypropeneHCID 521998p-Toluenesulfonic acid monohydrateHCID 18341276HCID 18341276, compound

Product 1

HCID 18341303HCID 18341303, compoundYield 889.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 2-bromo-N-(1(S)-hydroxymethyl-2-phenylethyl)acetamide (1.55 g, 5.45 mmol) and p-toluenesulfonic acid monohydrate (100 mg) in CH2Cl2 (50 mL) was added 2-methoxypropene (1.50 mL, 15.7 mmol) dropwise via syringe. After 15 minutes at ambient temperature, the resultant mixture was washed with 1M pH7 phosphate buffer (25 mL) and brine (25 mL), dried over Na2SO4, and concentrated to give a dark solid, which was triturated with MTBE/hex to provide 1.46 g (86%) of 3-(2-bromoacetyl)-2,2-dimethyl-4(S)-phenylmethyl-oxazolidine as a pale yellow solid.

Workup

  1. washthe resultant mixture was washed with 1M pH7 phosphate buffer (25 mL) and brine (25 mL)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. customto give a dark solid, which
  5. customwas triturated with MTBE/hex

Sources & evidence

ORD record
ord-3604e287c5604fd184bc1f438fcc387f
Source dataset
uspto-grants-2001_10
Patent number
US06306892B1

Reaction notes

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