تفاعل #487548

ord-a306553d7b024c76aa40148fcf6f7e78

معادلة التفاعل

O=C(Nc1ccc2c(c1)CCNC2)OCc1ccccc1
benzyl (1,2,3,4-tetrahydro-isoquinolin-6-yl)-carbamate
O=C([O-])O.[Na+]
sodium hydrogen carbonate
C=O
formalin
CC(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+]
sodium triacetoxyborohydride
O=C([O-])C(F)(F)F
trifluoroacetate
CN1CCc2cc(NC(=O)OCc3ccccc3)ccc2C1
benzyl (2-methyl-1,2,3,4-tetrahydro-isoquinolin-6-yl)-carbamate

المذيبات

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

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

الإجراء التجريبي

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.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US08741890B2uspto-grants-2014_06