2,6-Lutidine → (2S, 3S, 5R)-2-(3,4difluorophenyl)-3,5-dimethyl-2-morpholinol hydrobromide

HRID 265233Notes

Reaction equation

HRID 265233 reaction equation
[Br:1][CH:2]([CH3:13])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([F:11])=[C:7]([F:12])[CH:6]=1)=[O:4].C[C@@H](N)C[OH:17].[N:19]1C(C)=CC=[CH:21][C:20]=1[CH3:26]>C(#N)C>[BrH:1].[F:12][C:7]1[CH:6]=[C:5]([C@:3]2([OH:17])[O:4][CH2:21][C@@H:20]([CH3:26])[NH:19][C@H:2]2[CH3:13])[CH:10]=[CH:9][C:8]=1[F:11]

Participants

5

Reactant 3

HCID 79372,6-LutidineHCID 80308(R)-(-)-2-Amino-1-propanolHCID 152812742-Bromo-1-(3,4-difluorophenyl)propan-1-one

Product 1

HCID 67706270(2S, 3S, 5R)-2-(3,4difluorophenyl)-3,5-dimethyl-2-morpholinol hydrobromideYield 43.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-bromo-3',4'-difluoropropiophenone (47.3 g, 0.19 mole) in acetronitrile (100 ml) was added a solution of R-2-amino-1-propanol (Aldrich Chemical Co., Milwaukee, Wis. 53233) (15 g, 0.20 mole) and 2,6-lutidine (23.6 g, 0.22 mole) in acetonitrile (50 ml). The reaction was worked up as in Example 1 to give 26.9 g of (2S,3S,5R)-2-(3,4-difluorophenyl)-3,5-dimethyl-2-morpholinol hydrobromide.

Sources & evidence

ORD record
ord-829105790afa4231aa5f21ec1b0b9324
Source dataset
uspto-grants-1997_07
Patent number
US05648347

Reaction notes

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