Triethylamine → (2S)-1-{[tert-butyl(dimethyl)silyl]oxy}-4-fluoro-4-methylpentan-2-amine

HRID 1880518Notes

Reaction equation

[NH2:1][C@@H:2]([CH2:5][C:6]([F:9])([CH3:8])[CH3:7])[CH2:3][OH:4].[Si:10](Cl)([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11].C(N(CC)CC)C.[Cl-].[NH4+]>ClCCl.CN(C)C1C=CN=CC=1>[Si:10]([O:4][CH2:3][C@@H:2]([NH2:1])[CH2:5][C:6]([F:9])([CH3:8])[CH3:7])([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11]

Participants

Conditions

Temperature: 0 °C

Procedure

The amino alcohol (21.0 g) from Step 5 was dissolved in dichloromethane (300 mL) and the solution was cooled to 0° C. 4-(Dimethylamino)pyridine (0.051 g) and tert-butyldimethylsilyl chloride (21 g) were added followed by triethylamine (25 mL). The mixture was stirred at room temperature overnight. The reaction mixture was slowly poured into 0° C. saturated aqueous ammonium chloride and extracted with dichloromethane (3×300 mL). The organic layer was washed with brine, dried with sodium sulfate and the solvents were removed in vacuo to yield (2S)-1-{[tert-butyl(dimethyl)silyl]oxy}-4-fluoro-4-methylpentan-2-amine.

Workup

extractionextracted with dichloromethane (3×300 mL)
washThe organic layer was washed with brine
dry with materialdried with sodium sulfate
customthe solvents were removed in vacuo

Sources & evidence

ORD record: ord-b60c35a7d2514335b0488c2380412dcd
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08318748B2

Reaction notes

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