2-Methoxypropene → HCID 18341303, compound

HRID 613934Notes

Reaction equation

HRID 613934 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 pH 7 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. 1H NMR (DMSO-d6): δ 7.33-7.17 (m, 5H), 4.21-4.15 (m, 1H), 4.04, 3.86 (AB quartet, 2H, J=12.1 Hz), 3.79 (dd, 1H, J=4.8, 9.2 Hz), 3.71 (d, 1H, J=9.2 Hz), 2.99 (dd, 1H, J=5.0, 13.4 Hz), 2.70 (dd, 1H, J=9.2, 13.2 Hz), 1.55 (s, 3H), 1.38 (s, 3H). Anal. Calculated for C14H18NO2Br: C, 53.86; H, 5.81; N, 4.49; Br, 25.59. Found: C, 53.91; H, 5.82; N, 4.47; Br, 25.58.

Workup

  1. washthe resultant mixture was washed with 1M pH 7 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-b0b9dc82e36940f7864441b58cebbb28
Source dataset
uspto-grants-1999_12
Patent number
US06008243

Reaction notes

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