Reaction #487548

Reaction equation

benzyl (1,2,3,4-tetrahydro-isoquinolin-6-yl)-carbamate

sodium hydrogen carbonate

formalin

sodium triacetoxyborohydride

trifluoroacetate

→

benzyl (2-methyl-1,2,3,4-tetrahydro-isoquinolin-6-yl)-carbamate

Solvents

methanol

acetic acid

Conditions

Workup

1. 1
   workup.STIRRINGthe mixture is stirred for two hours
2. 2
   Extractionextracted three times with ethyl acetate
3. 3
   OtherThe combined organic phases are dried on sodium sulphate
4. 4
   Otherevaporated to dryness i.vac

Procedure

1.5 g (3.8 mmol) benzyl (1,2,3,4-tetrahydro-isoquinolin-6-yl)-carbamate (as the trifluoroacetate salt) are suspended in 8 ml of methanol and adjusted to pH 6 with acetic acid. 0.6 ml (8.5 mmol) formalin solution (37% in water) are added and the mixture is stirred for 30 minutes at RT. Then a total of 1.8 g (8.5 mmol) sodium triacetoxyborohydride are added batchwise and the mixture is stirred for two hours. The reaction mixture is poured onto sat. sodium hydrogen carbonate solution and extracted three times with ethyl acetate. The combined organic phases are dried on sodium sulphate and evaporated to dryness i.vac.

Source