Trifluoroacetic acid → (E)-1-(pyrrolidin-1-yl)-3-(1,2,3,4-tetrahydroisoquinolin-6-yl)prop-2-en-1-one trifluoro acetic acid

HRID 2174577Notes

Reaction equation

HRID 2174577 reaction equation
[O:1]=[C:2]([N:22]1[CH2:26][CH2:25][CH2:24][CH2:23]1)/[CH:3]=[CH:4]/[C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[CH2:11][N:10](C(OC(C)(C)C)=O)[CH2:9][CH2:8]2.[C:27]([OH:33])([C:29]([F:32])([F:31])[F:30])=[O:28]>C(Cl)Cl>[F:30][C:29]([F:32])([F:31])[C:27]([OH:33])=[O:28].[N:22]1([C:2](=[O:1])/[CH:3]=[CH:4]/[C:5]2[CH:6]=[C:7]3[C:12](=[CH:13][CH:14]=2)[CH2:11][NH:10][CH2:9][CH2:8]3)[CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 89602353(E)-tert-butyl 6-(3-oxo-3-(pyrrolidin-1-yl) prop-1-en-1-yl)-3,4-dihydroisoquinoline-2(1H)-carboxylate

Product 1

HCID 117690821(E)-1-(pyrrolidin-1-yl)-3-(1,2,3,4-tetrahydroisoquinolin-6-yl)prop-2-en-1-one trifluoro acetic acidYield 91.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 125c (400 mg, 1.12 mmol) in CH2Cl2 (4 ml) was treated with TFA (1.28 g, 11.21 mmol)) at 20-35° C. for 16 h. The progress of the reaction was monitored by TLC. After 16 h of stirring, the clear solution was concentrated under vacuum and the resultant solid was washed with diethyl ether to get the desired compound as a gummy liquid (380 mg, 91%). 1H NMR (400 MHz, DMSO-d6) δ 9.05 (bs, 2H), 7.58 (d, J=8.3 Hz, 2H), 7.43 (d, J=15.6 Hz, 1H), 7.25 (d, J=7.8 Hz, 1H), 6.99 (d, J=15.6 Hz, 1H), 4.32-4.24 (m, 2H), 3.63 (t, J=6.9 Hz, 2H), 3.39 (t, J=6.9 Hz, 4H), 3.01 (t, J=6.1 Hz, 2H), 1.98-1.89 (m, 2H), 1.88-1.76 (m, 2H).

Workup

  1. concentrationthe clear solution was concentrated under vacuum
  2. washthe resultant solid was washed with diethyl ether

Sources & evidence

ORD record
ord-ce09c55635214f0381551978eb37968b
Source dataset
uspto-grants-2015_06
Patent number
US09062002B2

Reaction notes

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