Hydrochloric Acid → (R)-3-methyl-1-(4'-(trifluoromethyl)biphenyl-4-yl)butan-1-amine hydrochloride

HRID 2173779Notes

Reaction equation

CC([S@]([NH:7][C@@H:8]([C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=2)=[CH:15][CH:14]=1)[CH2:9][CH:10]([CH3:12])[CH3:11])=O)(C)C.CO.[ClH:31]>CCOCC>[ClH:31].[CH3:11][CH:10]([CH3:12])[CH2:9][C@H:8]([C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][C:22]([C:25]([F:26])([F:27])[F:28])=[CH:21][CH:20]=2)=[CH:15][CH:14]=1)[NH2:7]

Participants

Conditions

Temperature: 0 °C

Procedure

A round bottom flask was charged with (R)-2-methyl-N-((R)-3-methyl-1-(4′-(trifluoromethyl)biphenyl-4-yl)butyl)propane-2-sulfinamide (47.5 g, 115.5 mmol) and methanol (300 mL). The mixture was cooled to 0° C. and 2.0N HCl in ether (150 mL) was added. The reaction was stirred for 20 minutes. The reaction was then concentrated under reduced pressure. Trituration with ether provided (R)-3-methyl-1-(4′-(trifluoromethyl)biphenyl-4-yl)butan-1-amine hydrochloride (35.3 g, 89%), as a white solid. 1H NMR (400 MHz, CD3OD, δ): 0.95 (d, 3H) 0.99 (d, J=6.44 Hz, 3H) 1.38-1.51 (m, 1H) 1.78-1.91 (m, 1H) 1.92-2.03 (m, 1H) 4.40 (dd, J=10.15, 5.66 Hz, 1H) 7.56-7.63 (m, 2H) 7.74-7.88 (m, 6H). MS (M+1): 291.2. [α]D=−11.9, c=1.8 (MeOH).

Workup

concentrationThe reaction was then concentrated under reduced pressure

Sources & evidence

ORD record: ord-f1d8cd7e4a614049a01779af434044bf
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09056834B2

Reaction notes

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