Formaldehyde → HCID 86654993, compound

HRID 400366Notes

Reaction equation

HRID 400366 reaction equation
[CH2:1]1[C:10]2[C:5](=[CH:6][C:7]([NH:11][C:12](=[O:21])[O:13][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:8][CH:9]=2)[CH2:4][CH2:3][NH:2]1.F[C:23](F)(F)C([O-])=O.C=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>CO.C(O)(=O)C>[CH3:23][N:2]1[CH2:3][CH2:4][C:5]2[C:10](=[CH:9][CH:8]=[C:7]([NH:11][C:12](=[O:21])[O:13][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:6]=2)[CH2:1]1

Participants

8

Reactant 5

HCID 712FormaldehydeHCID 84468TrifluoroacetateHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 86654994HCID 86654994, compound

Product 1

HCID 86654993HCID 86654993, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

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.

Workup

  1. stirringthe mixture is stirred for two hours
  2. extractionextracted three times with ethyl acetate
  3. customThe combined organic phases are dried on sodium sulphate
  4. customevaporated to dryness i.vac

Sources & evidence

ORD record
ord-a306553d7b024c76aa40148fcf6f7e78
Source dataset
uspto-grants-2014_06
Patent number
US08741890B2

Reaction notes

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