HCID 49834132, compound → HCID 68749897, compound

HRID 1614867Notes

Reaction equation

HRID 1614867 reaction equation
O=[C:2]1[CH2:6][CH2:5][C@@H:4]([C:7]2[CH:16]=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][CH:8]=2)[CH2:3]1.Cl.[F:18][C:19]1[CH:24]=[CH:23][C:22]([C@H:25]([NH2:27])[CH3:26])=[CH:21][C:20]=1[O:28][CH3:29]>>[F:18][C:19]1[CH:24]=[CH:23][C:22]([C@H:25]([NH:27][C@H:2]2[CH2:6][CH2:5][C@@H:4]([C:7]3[CH:16]=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][CH:8]=3)[CH2:3]2)[CH3:26])=[CH:21][C:20]=1[O:28][CH3:29]

Participants

3

Reactant 2

HCID 49834132HCID 49834132, compoundHCID 53484667(R)-1-(4-Fluoro-3-methoxyphenyl)ethanamine hydrochloride

Product 1

HCID 68749897HCID 68749897, compound

Procedure

General procedure B was followed using methyl 4-[(1R)-3-oxocyclopentyl]benzoate (preparation 32) as the ketone and (1R)-1-(4-fluoro-3-methoxyphenyl)ethylamine hydrochloride as the amine. The resulting isomers were separated by flash chromatography (gradient of 0-50% EtOAc in heptane containing 3% NEt3). The faster eluting peak was isolated to afford the title compound. 1H NMR (300 MHz, DMSO) 7.86 (d, J=8.3 Hz, 2H), 7.38 (d, J=8.3 Hz, 2H), 7.15 (dd, J=8.7, 1.8 Hz, 1H), 7.09 (dd, J=11.5, 8.3 Hz, 1H), 6.91-6.85 (m, 1H), 3.83 (2s, 6H), 3.80-3.70 (m, 1H), 3.05-2.86 (m, 2H), 2.22-1.52 (m, 5H), 1.41-1.27 (m, 1H), 1.23 (d, J=6.6 Hz, 3H).

Workup

  1. customThe resulting isomers were separated by flash chromatography (gradient of 0-50% EtOAc in heptane containing 3% NEt3)
  2. washThe faster eluting peak
  3. customwas isolated

Sources & evidence

ORD record
ord-94fb7062f41340d294753496f1f6ae72
Source dataset
uspto-grants-2014_07
Patent number
US08765676B2

Reaction notes

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