5-Azido-5,6,7,8-tetrahydronaphthalene-2-carboxylic acid methyl ester → (5-Amino-5,6,7,8-tetrahydronaphthalen-2-yl)methanol
Reaction equation
C[O:2][C:3]([C:5]1[CH:14]=[CH:13][C:12]2[CH:11]([N:15]=[N+]=[N-])[CH2:10][CH2:9][CH2:8][C:7]=2[CH:6]=1)=O>C1COCC1>[NH2:15][CH:11]1[CH2:10][CH2:9][CH2:8][C:7]2[CH:6]=[C:5]([CH2:3][OH:2])[CH:14]=[CH:13][C:12]1=2Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
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).