Reaktion #56668

ord-f153600557c0416791bf202cd4833cdf

Reaktionsgleichung

O
water
CCOC(=O)c1ccc([C@H]2CC[C@H](N)CC2)cc1
trans-ethyl 4-(4-aminocyclohexyl)benzoate
CCN(CC)CC
triethylamine
O=C(Cl)OCc1ccccc1
benzyl chloroformate
→
CCOC(=O)c1ccc([C@H]2CC[C@H](NC(=O)OCc3ccccc3)CC2)cc1
trans-Ethyl 4-(4-(N-benzyloxycarbonylamino)cyclohexyl)benzoate

Edukte

O
water
CCOC(=O)c1ccc([C@H]2CC[C@H](N)CC2)cc1
trans-ethyl 4-(4-aminocyclohexyl)benzoate
CCN(CC)CC
triethylamine
O=C(Cl)OCc1ccccc1
benzyl chloroformate

Reagenzien

Keine

Lösungsmittel

CN(C)C=O
dimethylformamide

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Extraktionextracted with ethyl acetate
  2. 2
    Sonstigedried
  3. 3
    Sonstigethe solvent is evaporated off
  4. 4
    SonstigeThe residue is purified by chromatography on a silica gel column
  5. 5
    Wascheneluting with an 8/2 cyclohexane/ethyl acetate mixture
  6. 6
    SonstigeThe compound of the title is obtained

Vorschrift

A mixture of 2.0 g (0.0008 mol) of trans-ethyl 4-(4-aminocyclohexyl)benzoate, 1.25 ml of triethylamine and 1.26 ml (0.0084 mol) of benzyl chloroformate at 95% in 40 ml of dimethylformamide is stirred at room temperature for 3 hours. The mixture is poured into water, extracted with ethyl acetate and dried, and the solvent is evaporated off. The residue is purified by chromatography on a silica gel column, eluting with an 8/2 cyclohexane/ethyl acetate mixture. The compound of the title is obtained.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07419974B2uspto-grants-2008_09