Benzyl Bromide → N-{(1R)-1-[(benzyloxy)methyl]-2-methylpropyl}-4-(trifluoromethyl)aniline

HRID 1360393Notes

Reaction equation

HRID 1360393 reaction equation
[H-].[Na+].[CH3:3][CH:4]([CH3:19])[C@@H:5]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=1)[CH2:6][OH:7].[CH2:20](Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CN(C)C=O>[CH2:20]([O:7][CH2:6][C@H:5]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([F:16])([F:17])[F:18])=[CH:11][CH:10]=1)[CH:4]([CH3:19])[CH3:3])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 66968920(2R)-3-methyl-2-{[4-(trifluoromethyl)phenyl]amino}butan-1-ol2×

Product 1

HCID 66969566N-{(1R)-1-[(benzyloxy)methyl]-2-methylpropyl}-4-(trifluoromethyl)aniline

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

Sodium hydride (10 mg) and (2R)-3-methyl-2-{[4-(trifluoromethyl)phenyl]amino}butan-1-ol (30 mg), which is the compound obtained in Step 1 of Example 2, were dissolved in dimethylformamide (1 mL), and then benzyl bromide (0.052 mL) was added. The mixture was stirred at 50° C. for 3 hrs, and the title compound (37.5 mg) was obtained by purification step A.

Sources & evidence

ORD record
ord-5f52b03e35b640fea26a351c6cb539fb
Source dataset
uspto-grants-2011_02
Patent number
US07879863B2

Reaction notes

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