Hydrochloric Acid → HCID 59543862, compound

HRID 1924010Notes

Reaction equation

HRID 1924010 reaction equation
[CH3:1][C@H:2]1[CH2:7][O:6][CH2:5][CH2:4][NH:3]1.[Br:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=O)=[CH:11][C:10]=1[F:17].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].Cl>ClC(Cl)C>[Br:8][C:9]1[CH:16]=[CH:15][C:12]([CH2:13][N:3]2[CH2:4][CH2:5][O:6][CH2:7][C@@H:2]2[CH3:1])=[CH:11][C:10]=1[F:17]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 27834114-Bromo-3-fluorobenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 12012220(3S)-3-methylmorpholine

Product 1

HCID 59543862HCID 59543862, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

(S)-3-Methylmorpholine (119 mg, 0.86 mmol), 4-bromo-3-fluorobenzaldehyde (175 mg, 0.86 mmol) triethylamine (132 μl, 0.95 mmol) and sodium triacetoxyborohydride (274 mg, 1.29 mmol) were dissolved in dichloroethane (2.5 ml). The mixture was stirred at ambient temperature under argon atmosphere for 24 h. Hydrochloric acid (1M) was added until pH 1-2. The mixture was washed with dichloromethane. The aqueous phase was made alkaline with KOH (1M, aq) and extracted with dichloromethane. The combined organic phases were dried over Na2SO4 and concentrated in vacuo to give (S)-4-(4-bromo-3-fluorobenzyl)-3-methylmorpholine (220 mg, 89%).

Workup

  1. washThe mixture was washed with dichloromethane
  2. extractionextracted with dichloromethane
  3. dry with materialThe combined organic phases were dried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d3ea7523ae474b5ebc9ff0bd57f093cb
Source dataset
uspto-grants-2012_05
Patent number
US08178529B2

Reaction notes

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