Sodium Bicarbonate → HCID 58124833, compound

HRID 1971653Notes

Reaction equation

HRID 1971653 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:15]2[C:10](=[CH:11][C:12]([O:19][CH3:20])=[C:13]([N+:16]([O-:18])=[O:17])[CH:14]=2)[CH2:9][CH2:8][N:7]=1)=[O:5])[CH3:2].[BH3-]C#N.[Na+].C([O-])(O)=O.[Na+]>C(O)(=O)C>[CH3:20][O:19][C:12]1[CH:11]=[C:10]2[C:15](=[CH:14][C:13]=1[N+:16]([O-:18])=[O:17])[CH:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[NH:7][CH2:8][CH2:9]2

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 58124932HCID 58124932, compound

Product 1

HCID 58124833HCID 58124833, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 34 g of 6-methoxy-7-nitro-3,4-dihydroisoquinoline-1-carboxylic acid ethyl ester in 300 ml of acetic acid was treated with 25 g NaCNBH3 (added in several portions). The mixture was stirred for 2 h. The reaction mixture was poured onto 300 g of solid NaHCO3 and 2 l of ice-water was carefully added with vigorous stirring. The product was extracted into dichloromethane. The organic layer was washed twice with water, dried and concentrated, to give 32g of essentially pure 6-methoxy-7-nitro-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid ethyl ester 1f. The compound is used as intermediate in the synthesis described in examples 1 and 2.

Workup

  1. additionwas carefully added with vigorous stirring
  2. extractionThe product was extracted into dichloromethane
  3. washThe organic layer was washed twice with water
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a98c1ecfd0de4ec587e1f3229d7d7720
Source dataset
uspto-grants-2013_04
Patent number
US08431564B2

Reaction notes

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