Triethylamine → HCID 131722216, compound

HRID 1275172Notes

Reaction equation

HRID 1275172 reaction equation
[Si](O[CH2:9][CH2:10][CH2:11][C@:12]1([C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[C:27]([Cl:32])[CH:26]=2)OCCN(C(OC(C)(C)C)=O)C1)(C(C)(C)C)(C)C.B1(Br)OC2[C:35](=CC=CC=2)[O:34]1.[OH-:43].[Na+].[CH2:45]([N:47](CC)CC)[CH3:46].[CH3:52][O:53][C:54]1[CH:55]=[C:56]([CH:60]=[C:61]([O:65][CH3:66])[C:62]=1[O:63][CH3:64])[C:57](Cl)=[O:58]>C(Cl)Cl.CN(C)C1C=CN=CC=1.O>[Cl:32][C:27]1[CH:26]=[C:25]([CH:12]2[C@@H:11]([CH2:10][CH2:9][CH2:35][OH:34])[O:43][CH2:46][CH2:45][N:47]2[C:57](=[O:58])[C:56]2[CH:55]=[C:54]([O:53][CH3:52])[C:62]([O:63][CH3:64])=[C:61]([O:65][CH3:66])[CH:60]=2)[CH:30]=[CH:29][C:28]=1[Cl:31]

Participants

9

Reactant 5

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 78282Benzoyl chloride, 3,4,5-trimethoxy-HCID 35523842-Bromo-1,3,2-benzodioxaboroleHCID 70111941HCID 70111941, compound

Product 1

HCID 131722216HCID 131722216, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Procedure

3.43 g (6.80 mmole) of (2R)-3-[4-t-butoxycarbonyl-2-(3,4-dichlorophenyl)morpholin-2-yl]-1-propanol t-butyldimethylsilyl ether [prepared as described in step (f) above] were dissolved in 60 ml of methylene chloride, and 2.98 g (15.0 mmole) of B-bromocatecholborane were added to the resulting solution. The mixture was then stirred at room temperature for 2 hours under a nitrogen atmosphere. At the end of this time, 60 ml of water were poured into the reaction mixture, which was then stirred for a further 2 hours. The mixture was then made basic by the addition of a 1 N aqueous solution of sodium hydroxide and then extracted with methylene chloride. The organic extract was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. The solvent was removed by distillation under reduced pressure. The resulting residue was dissolved in 40 ml of methylene chloride, and 1.23 ml (8.87 mmole) of triethylamine, 1.65 g (7.15 mmole) of 3,4,5-trimethoxybenzoyl chloride and 10 mg of 4-dimethylaminopyridine were added to the resulting solution. The mixture was then stirred at room temperature for 12 hours. At the end of this time, the reaction mixture was poured into water and extracted with methylene chloride. The organic extract was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate, and the solvent was removed by distillation under reduced pressure. The resulting residue was purified by silica gel column chromatography, using a 7:3 by volume mixture of methylene chloride and acetone as the eluent, to give 2.13 g of the title compound.

Workup

  1. stirringwas then stirred for a further 2 hours
  2. extractionextracted with methylene chloride
  3. extractionThe organic extract
  4. washwas washed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was removed by distillation under reduced pressure
  7. dissolutionThe resulting residue was dissolved in 40 ml of methylene chloride
  8. stirringThe mixture was then stirred at room temperature for 12 hours
  9. extractionextracted with methylene chloride
  10. extractionThe organic extract
  11. washwas washed with a saturated aqueous solution of sodium chloride
  12. dry with materialdried over anhydrous sodium sulfate
  13. customthe solvent was removed by distillation under reduced pressure
  14. customThe resulting residue was purified by silica gel column chromatography
  15. additionby volume mixture of methylene chloride and acetone as the eluent

Sources & evidence

ORD record
ord-663f8ad3ce49424580f733343c975727
Source dataset
uspto-grants-2000_12
Patent number
US06159967

Reaction notes

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