Methanol → HCID 10045493, compound

HRID 457272Notes

Reaction equation

[CH3:1][C:2]1[CH:3]=[C:4]([CH:25]=[C:26]([CH3:28])[CH:27]=1)[CH2:5][C:6]([NH2:24])([C:20]([F:23])([F:22])[F:21])[CH2:7][C:8]([C:11]1[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:12]=1[O:18]C)([CH3:10])[CH3:9].B(Br)(Br)Br.CO>C(Cl)Cl>[NH2:24][C:6]([CH2:5][C:4]1[CH:25]=[C:26]([CH3:28])[CH:27]=[C:2]([CH3:1])[CH:3]=1)([C:20]([F:23])([F:21])[F:22])[CH2:7][C:8]([C:11]1[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:12]=1[OH:18])([CH3:10])[CH3:9]

Participants

Conditions

Temperature: 0 °C

Procedure

To a room temperature solution of 23 mg (0.058 mmol) of 1-(3,5-dimethylbenzyl)-3-(5-fluoro-2-methoxyphenyl)-3-methyl-1-trifluoromethylbutylamine (Example 2) in 0.5 mL of CH2Cl2 was added 0.5 mL (0.5 mmol) of a 1 M solution of BBr3 in CH2Cl2. After 1 h, the reaction was cooled to 0° C. and MeOH was added. The reaction was concentrated in vacuo and partitioned between aqueous sodium bicarbonate and EtOAc. The aqueous layer was separated and extracted with EtOAc. The combined organic layers were dried (MgSO4), filtered and concentrated to afford an oil. The crude material was purified on a short silica gel column eluting with hexanes-EtOAc (95:5) to afford 7 mg (33%) of the title compound.

Workup

concentrationThe reaction was concentrated in vacuo
custompartitioned between aqueous sodium bicarbonate and EtOAc
customThe aqueous layer was separated
extractionextracted with EtOAc
dry with materialThe combined organic layers were dried (MgSO4)
filtrationfiltered
concentrationconcentrated
customto afford an oil
customThe crude material was purified on a short silica gel column
washeluting with hexanes-EtOAc (95:5)

Sources & evidence

ORD record: ord-37e53928e292480e9ab9a014fc334d86
Source dataset: uspto-grants-2007_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07186864B2

Reaction notes

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