Triethylamine → HCID 18319551, compound

HRID 1699394Notes

Reaction equation

HRID 1699394 reaction equation
[CH:1]([C:3]1[C:13]2[O:12][CH2:11][CH2:10][C:9]([C:14]([O:16][CH3:17])=[O:15])=[CH:8][C:7]=2[CH:6]=[CH:5][CH:4]=1)=O.Cl.[CH3:19][NH:20][CH3:21].C(N(CC)CC)C.[BH4-].[Na+]>CO.O1CCCC1>[CH3:19][N:20]([CH2:1][C:3]1[C:13]2[O:12][CH2:11][CH2:10][C:9]([C:14]([O:16][CH3:17])=[O:15])=[CH:8][C:7]=2[CH:6]=[CH:5][CH:4]=1)[CH3:21]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 4311764Sodium borohydrideHCID 18319504HCID 18319504, compound

Product 1

HCID 18319551HCID 18319551, compoundYield 65.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

The mixture of methyl 2,3-dihydro-9-formyl-1-benzoxepin-4-carboxylate (1.0 g), dimethylamine hydrochloride (0.7 g), triethylamine (1.2 ml) and 4 Å molecular sieves (1.0 g) in methanol (20 ml) and tetrahydrofuran (10 ml) was stirred at ambient temperature for 3 hours. To the mixture was added sodium borohydride (0.33 g) under ice-cooling and the mixture was stirred at ambient temperature for 20 hours. The solvent was removed by concentration. The residue was dissolved in a mixture of ethyl acetate and water and the mixture was adjusted to pH 1 with 6N hydrochloric acid. The separated aqueous layer was adjusted pH 10 with 20% aqueous potassium carbonate and extracted with a solution of ethyl acetate and tetrahydrofuran. The extract layer was washed with brine, dried over magnesium sulfate and evaporated to give methyl 2,3-dihydro-9-dimethylaminomethyl-1-benzoxepin-4-carboxylate (0.74 g).

Workup

  1. temperaturecooling
  2. customThe solvent was removed by concentration
  3. dissolutionThe residue was dissolved in a mixture of ethyl acetate and water
  4. extractionextracted with a solution of ethyl acetate and tetrahydrofuran
  5. washThe extract layer was washed with brine
  6. dry with materialdried over magnesium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-71741c662bc14a4ea7c98887d8ab7138
Source dataset
uspto-grants-2002_02
Patent number
US06346527B1

Reaction notes

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