Reaktion #60390

Reaktionsgleichung

5-azido-5,6,7,8-tetrahydro-naphthalene-2-carboxylic acid methyl ester

→

title compound

(5-amino-5,6,7,8-tetrahydro-naphthalen-2-yl)-methanol

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction was quenched with THF and H2O mixture (30 mL, THF:H2O=2:1)
2. 2
   workup.ADDITIONfollowed by the sequential addition of 5 N NaOH (10 mL) and H2O (100 mL)
3. 3
   Sonstigethe temperature of the reaction lower than 5° C
4. 4
   workup.STIRRINGThe reaction was stirred at RT for additional 5 h
5. 5
   FiltrationThe precipitate was filtered
6. 6
   Waschenwashed with THF

Vorschrift

A solution of 5-azido-5,6,7,8-tetrahydro-naphthalene-2-carboxylic acid methyl ester (35 g, 151 mmol, 1.0 eq) in THF (100 mL) was added dropwise in 30 min. The reaction was warmed to RT spontaneously and stirred at RT overnight. The reaction was quenched with THF and H2O mixture (30 mL, THF:H2O=2:1), followed by the sequential addition of 5 N NaOH (10 mL) and H2O (100 mL) while keeping the temperature of the reaction lower than 5° C. The reaction was stirred at RT for additional 5 h. The precipitate was filtered and washed with THF. The concentration of the filtrate afforded the title compound as a light yellow solid. MS (ESI, pos. ion) m/z: 161 (M−NH3+1).

Quelle