Reaktion #48672

ord-d84c6867d5d949f78021d1ce8021af7c

Reaktionsgleichung

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

Edukte

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

Reagenzien

Keine

Lösungsmittel

CC#N
acetonitrile

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Waschenwash with saturated aqueous sodium chloride
  2. 2
    TrocknenDry (magnesium sulfate)
  3. 3
    Filtrationfilter
  4. 4
    Einengenconcentrate
  5. 5
    SonstigePurify on silica gel
  6. 6
    Wascheneluting with 0:100 to 30:70 ethyl acetate

Vorschrift

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.

Quelle

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