Sodium Sulfate → (S)-2-Amino-6,6,6-trifluoro-5-phenyl-hexan-1-ol

HRID 1026111Notes

Reaction equation

[H-].[Al+3].[Li+].[H-].[H-].[H-].C[O:8][C:9](=O)[C@@H:10]([NH2:24])[CH2:11][CH2:12][CH:13]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:14]([F:17])([F:16])[F:15].S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[NH2:24][C@@H:10]([CH2:11][CH2:12][CH:13]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:14]([F:15])([F:16])[F:17])[CH2:9][OH:8]

Participants

Conditions

Temperature: 50 °C

Procedure

To a suspension of lithium aluminum hydride (0.267 g) in tetrahydrofuran (30 ml) was added a solution of (S)-2-amino-6,6,6-trifluoro-5-phenyl-hexanoic acid methyl ester (0.97 g) in tetrahydrofuran (3 ml) and the mixture was stirred for 2 hours at 50° C. Sodium sulphate solution (2M, 0.3 ml) was added and the mixture was filtered through Celite. The solvent was evaporated and the residue was purified by chromatography (column: Isolute® Flash-NH2 from Separtis; eluent: ethyl acetate/MeOH=98:2) to yield a light yellow liquid, (0.50 g, 57%); MS (ISP): 248.1 ((M+H)

Workup

filtrationthe mixture was filtered through Celite
customThe solvent was evaporated
customthe residue was purified by chromatography (column: Isolute® Flash-NH2 from Separtis; eluent: ethyl acetate/MeOH=98:2)
customto yield a light yellow liquid, (0.50 g, 57%)

Sources & evidence

ORD record: ord-e8461c26f53041d5b36ee4a5a7e4114b
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08729113B2

Reaction notes

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