HCID 58993555, compound → HCID 24785446, compound

HRID 391471Notes

Reaction equation

HRID 391471 reaction equation
[CH3:1][O:2][C:3]1[CH:30]=[CH:29][C:28]([C:31]2[CH:36]=[CH:35][N:34]=[CH:33][CH:32]=2)=[CH:27][C:4]=1[CH2:5][O:6][CH2:7][C:8]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:13][CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10][CH2:9]1.FC(F)(F)C(O)=O.CN(C)C>FC(F)(F)C(O)=O>[CH3:1][O:2][C:3]1[CH:30]=[CH:29][C:28]([C:31]2[CH:36]=[CH:35][N:34]=[CH:33][CH:32]=2)=[CH:27][C:4]=1[CH2:5][O:6][CH2:7][C:8]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:9][CH2:10][NH:11][CH2:12][CH2:13]1

Participants

4

Reactant 2

HCID 58993555HCID 58993555, compoundHCID 86615909HCID 86615909, compound

Product 1

HCID 24785446HCID 24785446, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

tert-Butyl 4-((2-methoxy-5-(pyridin-4-yl)benzyloxy)methyl)-4-phenylpiperidine-1-carboxylate (26 mg, 0.053 mmol) was dissolved in trifluoroacetic acid (33% in dichloromethane, 4 mL) and stirred for 1 h. The reaction was concentrated and purified by column chromatography (5% methanol/dichloromethane/2% trimethylamine in ethanol→10% methanol/dichloromethane/2% trimethylamine in ethanol) to give 30.7 mg (quant.) as a colorless oil. The product was tainted with trimethylamine 2,2,2-trifluoroacetate. 1H NMR (500 MHz, CDCl3) δ ppm 13.28 (bs, 2H), 9.55 (m, 2H), 8.71 (d, J=5.2 Hz, 2H), 7.79 (d, J=5.2 Hz, 2H), 7.60 (m, 2H), 7.34 (m, 4H), 7.26 (m, 1H), 6.94 (d, J=8.6, 1H), 4.48 (s, 2H), 3.84 (s, 3H), 3.49 (s, 2H), 3.31 (m, 2H); 13C NMR (126 MHz, CDCl3) δ ppm 159.1, 154.0, 144.0, 140.5, 129.2, 128.6, 127.7, 127.4, 127.2, 126.9, 122.5, 110.8, 80.0, 67.5, 55.7, 41.2, 40.6. Mass spec.: 389.33 (MH)+. Accurate mass spec.: m/z 389.2228 [MH]+, Δ=0.3 ppm.

Workup

  1. concentrationThe reaction was concentrated
  2. custompurified by column chromatography (5% methanol/dichloromethane/2% trimethylamine in ethanol→10% methanol/dichloromethane/2% trimethylamine in ethanol)
  3. customto give 30.7 mg (quant.) as a colorless oil

Sources & evidence

ORD record
ord-bf95a7f94dc044e5b3e1fefe28f0ace3
Source dataset
uspto-grants-2013_02
Patent number
US08383821B2

Reaction notes

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