Reaction #48672

ord-d84c6867d5d949f78021d1ce8021af7c

Reaction equation

CCOC(C)=O
ethyl acetate
CC(C)(C)OC(=O)N[C@H](CO)COCc1ccccc1
((R)-2-benzyloxy-1-hydroxymethylethyl)-carbamic acid tert-butyl ester
C=C(c1ccccc1)c1ccccc1
1,1-diphenylethylene
O=C1CCC(=O)N1I
N-iodosuccinimide
→
CC(C)(C)OC(=O)N[C@@H](COCc1ccccc1)COC(CI)(c1ccccc1)c1ccccc1
desired compound
CC(C)(C)OC(=O)N[C@@H](COCc1ccccc1)COC(CI)(c1ccccc1)c1ccccc1
[(S)-2-benzyloxy-1-(2-iodo-1,1-diphenylethoxymethyl)-ethyl]-carbamic acid tert-butyl ester

Reactants

CCOC(C)=O
ethyl acetate
CC(C)(C)OC(=O)N[C@H](CO)COCc1ccccc1
((R)-2-benzyloxy-1-hydroxymethylethyl)-carbamic acid tert-butyl ester
C=C(c1ccccc1)c1ccccc1
1,1-diphenylethylene
O=C1CCC(=O)N1I
N-iodosuccinimide

Reagents

None

Solvents

CC#N
acetonitrile

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Washwash with saturated aqueous sodium chloride
  2. 2
    DryingDry (magnesium sulfate)
  3. 3
    Filtrationfilter
  4. 4
    Concentrationconcentrate
  5. 5
    OtherPurify on silica gel
  6. 6
    Washeluting with 0:100 to 30:70 ethyl acetate

Procedure

Dissolve ((R)-2-benzyloxy-1-hydroxymethylethyl)-carbamic acid tert-butyl ester (1.0 g, 3.55 mmol) and 1,1-diphenylethylene (0.534 g, 2.96 mmol) in acetonitrile (20 mL). Add N-iodosuccinimide (0.800 g, 3.55 mmol) and stir at room temperature 72 hours. Pour into ethyl acetate and wash with saturated aqueous sodium chloride. Dry (magnesium sulfate), filter and concentrate. Purify on silica gel, eluting with 0:100 to 30:70 ethyl acetate:hexanes to give the desired compound.

Source

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