Methanol → HCID 89813562, compound

HRID 2172282Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[C:12]1[CH:21]=[CH:20][CH:19]=[C:18]2[C:13]=1[CH2:14][CH2:15][N:16](C(OC(C)(C)C)=O)[CH2:17]2.CO.C([Cl:34])(=O)C>C1COCC1>[ClH:34].[Br:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[C:12]1[CH:21]=[CH:20][CH:19]=[C:18]2[C:13]=1[CH2:14][CH2:15][NH:16][CH2:17]2

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of tert-butyl 5-(2-bromo-4-(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate (2.73 g, 5.98 mmol) in 12 mL THF was treated with methanol (2.421 ml, 59.8 mmol) and was cooled to 0° C. Acetyl chloride (4.25 ml, 59.8 mmol) was added, and the reaction mixture was allowed to stir overnight. LC/MS showed mostly product, so the reaction mixture was concentrated yielding 5-(2-bromo-4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline hydrochloride (2.32 g, 5.91 mmol). [M+H]+=357.9.

Workup

concentrationso the reaction mixture was concentrated

Sources & evidence

ORD record: ord-a40b1331a36b48e98c9f85465cd91af1
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09051311B2

Reaction notes

Loading…