2-Methoxypropene → HCID 18341303, compound

HRID 2300009Notes

Reaction equation

HRID 2300009 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. 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 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-8015a5ec21664e4c9f2577d3bde1b78c
Source dataset
uspto-grants-2002_12
Patent number
US06495699B2

Reaction notes

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