Trifluoroacetic acid → 1-((S)-4-(3,4-dichlorophenyl)-3,4-dihydronaphthalen-2-yl)ethanamine

HRID 556164Notes

Reaction equation

HRID 556164 reaction equation
[NH2:1][CH:2]([CH:4]1[CH2:13][C@@H:12]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[C:16]([Cl:21])[CH:15]=2)[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]1O)[CH3:3].C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:21][C:16]1[CH:15]=[C:14]([C@H:12]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH:5]=[C:4]([CH:2]([NH2:1])[CH3:3])[CH2:13]2)[CH:19]=[CH:18][C:17]=1[Cl:20]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58950758(4S)-2-(1-aminoethyl)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydronaphthalen-1-ol

Product 1

HCID 589507391-((S)-4-(3,4-dichlorophenyl)-3,4-dihydronaphthalen-2-yl)ethanamineYield 81.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 43 (400 mg, 1.19 mmol) in CH2Cl2 (5 mL) was added TFA (5 mL). The reaction mixture was stirred for 2 h before being concentrated. The residue was subjected to reverse phase column chromatography (CH3CN/H2O/0.1% Formic acid=5% to 100%) to give 1-((S)-4-(3,4-dichlorophenyl)-3,4-dihydronaphthalen-2-yl)ethanamine (0.31 g, 77.5%) as a mixture of two diastereomers (45 and 46).

Workup

  1. concentrationbefore being concentrated

Sources & evidence

ORD record
ord-0d2a8cc0a1004ed5bdab9ebb01e5a800
Source dataset
uspto-grants-2011_11
Patent number
US08053603B2

Reaction notes

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