p-Toluenesulfonic acid monohydrate → (S)-tert-butyl 1-hydroxybut-3-en-2-ylcarbamate

HRID 711999Notes

Reaction equation

HRID 711999 reaction equation
CC1(C)[N:6]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[C@@H:5]([CH:14]=[CH2:15])[CH2:4][O:3]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO.C([O-])(O)=O.[Na+]>[OH:3][CH2:4][C@@H:5]([NH:6][C:7](=[O:8])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH:14]=[CH2:15]

Participants

5

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 11020618tert-Butyl (4S)-4-ethenyl-2,2-dimethyl-1,3-oxazolidine-3-carboxylate

Product 1

HCID 11041481(S)-tert-butyl 1-hydroxybut-3-en-2-ylcarbamateYield 76%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of tert-butyl (4S)-2,2-dimethyl-4-vinyl-1,3-oxazolidine-3-carboxylate (1.90 g, 8.36 mmol) in methanol (83 mL) was added p-toluenesulfonic acid monohydrate (0.80 g, 4.2 mmol) at 0° C. The mixture was slowly warmed to room temperature overnight. The reaction mixture was diluted with saturated NaHCO3 solution, concentrated, and then diluted with ethyl acetate. The organic layer was washed with sat. NaHCO3 (2×) and brine, dried over Na2SO4, filtered and concentrated to give the desired product as colorless oil (1.187 g, 76%). 1H NMR (400 MHz, CDCl3) δ 5.81 (1H, m), 5.25 (2H, m), 4.90 (1H, m), 4.25 (1H, br s), 3.67 (2H, m), 1.45 (9H, s) ppm.

Workup

  1. concentrationconcentrated
  2. additiondiluted with ethyl acetate
  3. washThe organic layer was washed with sat. NaHCO3 (2×) and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ccef6943f9134345a3d6f95c5d259238
Source dataset
uspto-grants-2015_11
Patent number
US09181271B2

Reaction notes

Loading…