Reaktion #53916

ord-29e6230aee9c4456978ce0d50f9c6058

Reaktionsgleichung

CN(C(=O)OC(C)(C)C)[C@H]1CC[C@H](C#CCO)CC1
trans-[4-(3-Hydroxy-prop-1-ynyl)-cyclohexyl]-methyl-carbamic acid tert-butyl ester
→
CN(C(=O)OC(C)(C)C)[C@H]1CC[C@H](CCCO)CC1
trans-[4-(3-Hydroxy-propyl)-cyclohexyl]-methyl-carbamic acid tert-butyl ester
Ausbeute 101.4%

Edukte

CN(C(=O)OC(C)(C)C)[C@H]1CC[C@H](C#CCO)CC1
trans-[4-(3-Hydroxy-prop-1-ynyl)-cyclohexyl]-methyl-carbamic acid tert-butyl ester

Reagenzien

O.[O]=[Pt]=[O]
PtO2.H2O

Lösungsmittel

CCO
ethanol

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Sonstigefor 7 h
  2. 2
    FiltrationThe reaction was filtered (Celite)
  3. 3
    Sonstigeevaporated

Vorschrift

A suspension of 3.4 g (12.72 mmol) of trans-[4-(3-Hydroxy-prop-1-ynyl)-cyclohexyl]-methyl-carbamic acid tert-butyl ester in 125 ml ethanol and 810 mg of PtO2.H2O was hydrogenated (1 atm) for 7 h. The reaction was filtered (Celite) and evaporated to give 3.5 g (quantitative) of trans-[4-(3-Hydroxy-propyl)-cyclohexyl]-methyl-carbamic acid tert-butyl ester, MS: 271 (MH).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06858651B2uspto-grants-2005_02