(+)-1-(1-Naphthyl)ethylamine → HCID 69669913, compound

HRID 1627073Notes

Reaction equation

HRID 1627073 reaction equation
C[O:2][C:3](=[O:22])[CH2:4][CH2:5][C:6]1[CH:11]=[C:10]([C@@H:12]2[CH2:16][CH2:15][C:14](=O)[CH2:13]2)[CH:9]=[CH:8][C:7]=1[C:18]([F:21])([F:20])[F:19].[C:23]1([C@H:33]([NH2:35])[CH3:34])[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=[CH:25][CH:24]=1>>[C:23]1([C@H:33]([NH:35][CH:14]2[CH2:15][CH2:16][C@@H:12]([C:10]3[CH:9]=[CH:8][C:7]([C:18]([F:19])([F:21])[F:20])=[C:6]([CH2:5][CH2:4][C:3]([OH:2])=[O:22])[CH:11]=3)[CH2:13]2)[CH3:34])[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=[CH:25][CH:24]=1

Participants

3

Reactant 2

HCID 2724264(+)-1-(1-Naphthyl)ethylamineHCID 49834739HCID 49834739, compound

Product 1

HCID 69669913HCID 69669913, compound

Procedure

General procedure A was followed using 3-[5-((1R)-3-oxo-cyclopentyl)-2-trifluoromethyl-phenyl]-propionic acid methyl ester (preparation 16) as the ketone and (R)-1-naphthalen-1-yl-ethylamine as the amine. The resulting mixture of isomeric esters was purified and separated by flash chromatography. The faster eluting peak was isolated and subjected to hydrolysis following general procedure B to afford the title compound. 1H NMR (600 MHz, DMSO) δ 8.30 (d, J=8.2 Hz, 1H), 7.93 (d, J=8.0 Hz, 1H), 7.84-7.75 (m, 2H), 7.59-7.48 (m, 4H), 7.41-7.17 (m, 2H), 4.78 (s, 1H), 3.35-3.06 (m, 2H), 2.99-2.88 (m, 2H), 2.55-2.42 (m, 2H), 2.24-1.67 (m, 4H), 1.63-1.39 (m, 5H).

Workup

  1. customwas purified
  2. customseparated by flash chromatography
  3. washThe faster eluting peak
  4. customwas isolated
  5. customsubjected to hydrolysis

Sources & evidence

ORD record
ord-9f90177d14954d018f4406c0c9e8c1b9
Source dataset
uspto-grants-2014_07
Patent number
US08785494B2

Reaction notes

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