Reaction #48683

ord-bffe4dffcbdc41dca34b21a93476b393

Reaction equation

CCOC(C)=O
ethyl acetate
O=C1CCC(=O)N1I
N-iodosuccinimide
CC(C)(C)OC(=O)N[C@H](CO)COCc1ccccc1
((R)-2-benzyloxy-1-hydroxymethylethyl)-carbamic acid tert-butyl ester
C=COCC(C)(C)C
2,2-dimethyl-1-vinyloxypropane
→
CC(C)(C)COC(OCCI)[C@H](COCc1ccccc1)NC(=O)OC(C)(C)C
desired compound
Yield 84.2%
CC(C)(C)COC(OCCI)[C@H](COCc1ccccc1)NC(=O)OC(C)(C)C
{(S)-2-benzyloxy-1-[1-(2,2-dimethylpropoxy)-2-iodoethoxymethyl]-ethyl}-carbamic acid tert-butyl ester
Yield 84.2%

Reactants

CCOC(C)=O
ethyl acetate
O=C1CCC(=O)N1I
N-iodosuccinimide
CC(C)(C)OC(=O)N[C@H](CO)COCc1ccccc1
((R)-2-benzyloxy-1-hydroxymethylethyl)-carbamic acid tert-butyl ester
C=COCC(C)(C)C
2,2-dimethyl-1-vinyloxypropane

Reagents

None

Solvents

CC#N
acetonitrile

Conditions

Temperature
60°CELSIUS
Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    TemperatureCool to room temperature
  2. 2
    WashWash with water and saturated aqueous sodium chloride
  3. 3
    DryingDry (magnesium sulfate)
  4. 4
    Filtrationfilter
  5. 5
    Concentrationconcentrate
  6. 6
    Otherpurify
  7. 7
    Wash(silica gel chromatography, eluting with 0:100 to 10:90 ethyl acetate:hexanes)

Procedure

Add N-iodosuccinimide (14.19 g, 74.63 mmol) to ((R)-2-benzyloxy-1-hydroxymethylethyl)-carbamic acid tert-butyl ester (15.00 g, 53.30 mmol) and 2,2-dimethyl-1-vinyloxypropane (9.13 g, 79.96 mmol) in acetonitrile (267 mL) at room temperature. Heat to 60° C. under nitrogen for 2 hours. Cool to room temperature and dilute with ethyl acetate. Wash with water and saturated aqueous sodium chloride. Dry (magnesium sulfate), filter, concentrate and purify (silica gel chromatography, eluting with 0:100 to 10:90 ethyl acetate:hexanes) to give the desired compound as an oil (23.4 g 84.2%).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07745438B2uspto-grants-2010_06