Formic Acid → 1-((S)-4-(3,4-dichlorophenyl)-3,4-dihydronaphthalen-2-yl)-N,N-dimethylethanamine

HRID 556162Notes

Reaction equation

HRID 556162 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=[C:11]([CH:19]([NH:21][CH3:22])[CH3:20])[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].C=O.[CH:25](O)=O>CO>[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=[C:11]([CH:19]([N:21]([CH3:25])[CH3:22])[CH3:20])[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 3

HCID 284Formic AcidHCID 712FormaldehydeHCID 589507521-((S)-4-(3,4-dichlorophenyl)-3,4-dihydronaphthalen-2-yl)-N-methylethanamine

Product 1

HCID 589507491-((S)-4-(3,4-dichlorophenyl)-3,4-dihydronaphthalen-2-yl)-N,N-dimethylethanamineYield 91%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 47 (200 mg, 0.60 mmol) in MeOH (5 mL) was added HCHO (35 mg, 37%, 1.20 mml), HCO2H (0.3 mL) and NaB(CN)H3 (75 mg, 1.20 mmol). The reaction mixture was stirred for 20 min before being concentrated. The residue was dissolved in MeOH (2 mL) and subjected to reverse phase column chromatography (CH3CN/H2O/0.1% formic acid=5% to 100%) to give 48 (188 mg, 91%). 1H NMR (400 MHz, CDCl3)δ 7.34 (d, J=8.4 Hz, 1 H), 7.25 (m, 2 H), 7.20 (m, 2 H) 7.12 (m, 2 H), 7.0 (dd, J=2.0, 8.4 Hz, 1 H), 6.83 (d, J=7.6Hz, 1 H), 6.40 (s, 1 H), 4.10 (t, J=8.4 Hz, 1 H), 2.65 (d, t, J=6.4, 13.2 Hz, 1 H), 2.65 (dd, J=6.8, 16.4 Hz, 1 H), 2.54 (dd, J=9.2, 16.4 Hz, 1 H), 2.21 (s, 6 H), 1.01 (d, J=6.8 Hz, 1 H); 13C NMR (100 m Hz, CDCl3)δ 144.87, 142.04, 136.44, 134.67, 132.42, 130.61, 130.45, 128.16, 127.78, 127.53, 177.43, 126.61, 124.19, 124.12, 67.03, 43.72, 43.83, 43.50, 32.36, 16.45; ESI MS m/z 346.1

Workup

  1. concentrationbefore being concentrated
  2. dissolutionThe residue was dissolved in MeOH (2 mL)

Sources & evidence

ORD record
ord-aa5b9c53fdbc40308867581d89b4445f
Source dataset
uspto-grants-2011_11
Patent number
US08053603B2

Reaction notes

Loading…