Hydrochloric Acid → 3,3,3-Trifluoro-2-(trifluoromethyl)-1-(hydroxymethyl)propylamine
Reaction equation
[BH4-].[Li+].C([O:5][C:6](=O)[CH:7]([NH2:17])[CH:8]([C:13]([F:16])([F:15])[F:14])[C:9]([F:12])([F:11])[F:10])C.Cl>C1COCC1>[F:10][C:9]([F:11])([F:12])[CH:8]([C:13]([F:14])([F:15])[F:16])[CH:7]([NH2:17])[CH2:6][OH:5]Participants
Procedure
A solution of lithium borohydride (2M THF, 19.8 mL) was added to a solution of 2-amino-4,4,4-trifluoro-3-trifluoromethyl-butyric acid ethyl ester (5 g, 19.8 mmol), prepared as described (J. Med Chem. 1981, 24, 1043-1047), in THF (80 mL) at 25° C. and was stirred for 4 h. 2M HCl was added to the reaction mixture very carefully until a pH less than 2. The organic solvent was removed in vacuo and the aqueous layer was neutralized with sat NaHCO3 until pH=7. The aqueous layer was extracted with EtOAc (2×50 mL) and the organic extracts were dried over Na2SO4 and concentrated to provide 3,3,3-trifluoro-2-(trifluoromethyl)-1-(hydroxymethyl)propylamine as a yellow oil (3.2 g, 77% yield). The crude oil was of sufficient purity to utilize in the subsequent reaction.
Workup
- customprepared
- customThe organic solvent was removed in vacuo
- extractionThe aqueous layer was extracted with EtOAc (2×50 mL)
- dry with materialthe organic extracts were dried over Na2SO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-f58477bf4c3c4d5ebae2146e364a6983
- Source dataset
- uspto-grants-2010_12
- Patent number
- US07858658B2
Reaction notes
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