Triethylamine → (S)-4-(4-Bromo-2,5-difluorobenzyl)-3-methylmorpholine

HRID 1924013Notes

Reaction equation

HRID 1924013 reaction equation
[Br:1][C:2]1[C:9]([F:10])=[CH:8][C:5]([CH:6]=O)=[C:4]([F:11])[CH:3]=1.Cl.[CH3:13][C@H:14]1[CH2:19][O:18][CH2:17][CH2:16][NH:15]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(N(CC)CC)C.C([O-])(O)=O.[Na+]>ClC(Cl)C>[Br:1][C:2]1[C:9]([F:10])=[CH:8][C:5]([CH2:6][N:15]2[CH2:16][CH2:17][O:18][CH2:19][C@@H:14]2[CH3:13])=[C:4]([F:11])[CH:3]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 224890814-Bromo-2,5-difluorobenzaldehydeHCID 53486469(3S)-3-methylmorpholine hydrochloride

Product 1

HCID 59543858(S)-4-(4-Bromo-2,5-difluorobenzyl)-3-methylmorpholineYield 94.1%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

4-Bromo-2,5-difluorobenzaldehyde (331 mg, 1.5 mmol), (S)-3-methylmorpholine hydrochloride (206 mg, 1.50 mmol) and sodium triacetoxyborohydride (461 mg, 2.18 mmol) were mixed in dichloroethane (5 mL). Triethylamine (0.230 mL, 1.65 mmol) was added and the resulting mixture was stirred at RT under argon atmosphere for 24 h. NaHCO3 (25 mL) was added and the mixture was extracted with dichloromethane (3×25 mL). The combined organic extracts were dried over MgSO4, filtered and concentrated to give (S)-4-(4-bromo-2,5-difluorobenzyl)-3-methylmorpholine (432 mg, 94%) as a solid.

Workup

  1. extractionthe mixture was extracted with dichloromethane (3×25 mL)
  2. dry with materialThe combined organic extracts were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-7db1490fb085401faa18fa6064368682
Source dataset
uspto-grants-2012_05
Patent number
US08178529B2

Reaction notes

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