Water → HCID 18703992, compound

HRID 2288066Notes

Reaction equation

HRID 2288066 reaction equation
[CH3:1][C:2]1([CH3:17])[CH2:11][C:10]2[C:9]([C:12]([O:14][CH3:15])=[O:13])=[CH:8][CH:7]=[CH:6][C:5]=2[C:4](=O)[CH2:3]1.C([O-])(=O)C.[NH4+].C([BH3-])#[N:24].[Na+].O>CO>[NH2:24][CH:4]1[CH2:3][C:2]([CH3:17])([CH3:1])[CH2:11][C:10]2[C:9]([C:12]([O:14][CH3:15])=[O:13])=[CH:8][CH:7]=[CH:6][C:5]1=2

Participants

6

Reactant 4

HCID 962WaterHCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 12284902Methyl 5,6,7,8-tetrahydro-7,7-dimethyl-5-oxo-1-naphthalenecarboxylate

Product 1

HCID 18703992HCID 18703992, compoundYield 95.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 3.0 g (13 mmol) of methyl 7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-1-naphthalenecarboxylate (J. Org. Chem. 17 (1976), 2918) in 45 ml of methanol was treated with 10 g (130 mmol) of ammonium acetate and 5.7 g (90 mmol) of sodium cyanoborohydride and heated at 60° C. for 20 hrs. After addition of 10 ml of water, the mixture was completely concentrated in vacuo and the residue was taken up in EA and aqueous ammonia. The organic phase was washed with water, dried over magnesium sulfate and concentrated in a rotary evaporator, and 2.9 g of methyl 5-amino-7,7-dimethyl-5,6,7,8-tetrahydro-1-naphthalenecarboxylate were obtained.

Workup

  1. concentrationthe mixture was completely concentrated in vacuo
  2. washThe organic phase was washed with water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in a rotary evaporator

Sources & evidence

ORD record
ord-30d93a14d7c94eb0ae0419dbf8fe14a2
Source dataset
uspto-grants-2000_07
Patent number
US06087399

Reaction notes

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