Triethylamine → HCID 19735100, compound

HRID 326599Notes

Reaction equation

HRID 326599 reaction equation
C(Cl)(=O)OCC.[C:7]([C:10]1[CH:11]=[CH:12][C:13]2[O:18][C:17]([CH3:20])([CH3:19])[N:16]=[C:15]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=3)[C:14]=2[CH:27]=1)(O)=[O:8].C(N(CC)CC)C>O1CCCC1>[OH:8][CH2:7][C:10]1[CH:11]=[CH:12][C:13]2[O:18][C:17]([CH3:20])([CH3:19])[N:16]=[C:15]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=3)[C:14]=2[CH:27]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 19735117HCID 19735117, compound

Product 1

HCID 19735100HCID 19735100, compoundYield 57.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl chlorocarbonate(80 mg) was added to a solution of Compound 113 (200 mg) and triethylamine (0.10 ml) in anhydrous tetrahydrofuran (1 ml) at -15° C. under an argon atmosphere and the mixture was stirred at -15° to -10° C. for 30 minutes. The resulting precipitate was filtered off and the filtrate was added to a solution of sodium borohydride (67 mg) in water (0.7 ml) at 10° C. After completion of the addition, the mixture was allowed to warm to room temperature and stirred for 3 hours. The mixture was extracted by addition of water and ethyl acetate. The organic layer was washed with saturated saline solution and dried over anhydrous magnesium sulfate. The solvent was distilled off and the residue was purified by silica gel column chromatography to obtain 6-hydroxymethyl-2,2-dimethyl-4-(2-pyridyl)-2H-1,3-benzoxazine (110 mg) (Compound 115). Likewise, Compound 145 was prepared from Compound 114.

Workup

  1. filtrationThe resulting precipitate was filtered off
  2. additionthe filtrate was added to a solution of sodium borohydride (67 mg) in water (0.7 ml) at 10° C
  3. additionAfter completion of the addition
  4. stirringstirred for 3 hours
  5. extractionThe mixture was extracted by addition of water and ethyl acetate
  6. washThe organic layer was washed with saturated saline solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationThe solvent was distilled off
  9. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-533a46c28dbc4d8d8ba0041f6f8413a9
Source dataset
uspto-grants-1993_12
Patent number
US05270308

Reaction notes

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