1,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)- → tert-butyl(3S)-3-{[((3aR,4S,6aS)-2-{[3-(trifluoromethyl)phenyl]sulfonyl}octahydrocyclopenta[c]pyrrol-4-yl)amino]carbonyl}-3,4-dihydroisoquinoline-2(1H)-carboxylate

HRID 2363585Notes

Reaction equation

HRID 2363585 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12]CC[C@H:9]1[C:13](O)=[O:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].[F:16][C:17]([F:37])([F:36])[C:18]1[CH:19]=[C:20]([S:24]([N:27]2[CH2:31][C@@H:30]3[C@@H:32]([NH2:35])[CH2:33][CH2:34][C@@H:29]3[CH2:28]2)(=[O:26])=[O:25])[CH:21]=[CH:22][CH:23]=1.F[C:39](F)(F)[C:40]1[CH:41]=[C:42](S(N2C[C@H]3[C@H](N)CC[C@H]3C2)(=O)=O)[CH:43]=[CH:44][CH:45]=1>>[F:37][C:17]([F:16])([F:36])[C:18]1[CH:19]=[C:20]([S:24]([N:27]2[CH2:31][C@@H:30]3[C@@H:32]([NH:35][C:13]([C@@H:9]4[CH2:39][C:40]5[C:45](=[CH:44][CH:43]=[CH:42][CH:41]=5)[CH2:12][N:8]4[C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])=[O:14])[CH2:33][CH2:34][C@@H:29]3[CH2:28]2)(=[O:25])=[O:26])[CH:21]=[CH:22][CH:23]=1

Participants

4

Reactant 3

HCID 850831,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)-HCID 66590521(3aR,4S,6aS)-2-(3-(trifluoromethyl)phenylsulfonyl)octahydrocyclopenta[c]pyrrol-4-amineHCID 66590613(3aS,4R,6aR)-2-(3-(Trifluoromethyl)phenylsulfonyl)octahydrocyclopenta[c]pyrrol-4-amine

Product 1

HCID 66590757tert-butyl(3S)-3-{[((3aR,4S,6aS)-2-{[3-(trifluoromethyl)phenyl]sulfonyl}octahydrocyclopenta[c]pyrrol-4-yl)amino]carbonyl}-3,4-dihydroisoquinoline-2(1H)-carboxylate

Procedure

The title compound was prepared by substituting (S)-2-(tert-butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid for (S)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid and (3aR,4S,6aS)-2-(3-(trifluoromethyl)phenylsulfonyl)octahydrocyclopenta[c]pyrrol-4-amine from Step D of Example 252 for (3aS,4R,6aR)-2-(3-(trifluoromethyl)phenylsulfonyl)octahydrocyclopenta[c]pyrrol-4-amine in the procedure described in Example 266: 1H NMR (500 MHz, pyridine-d5, temperature 90° C.) δ ppm 8.26-8.27 (bs, 1H), 8.08-8.10 (m, 1H), 7.81-7.84 (m, 1H), 7.62 (t, J=7.8 Hz, 1H), 7.29-7.36 (m, 1H), 7.12-7.14 (m, 2H), 7.08-7.11 (m, 2H), 4.83-5.02 (m, 1H), 4.78 (d, J=15.6 Hz, 1H), 4.67 (d, J=15.6 Hz, 1H), 3.90-3.97 (m, 1H), 3.52 (dd, J=10.1, 3.3 Hz, 1H), 3.30 (dd, J=15.3, 4.8 Hz, 1H), 3.14 (dd, J=9.9, 7.8 Hz, 1H), 3.11 (dd, J=15.4, 6.3 Hz, 1H), 3.04-3.08 (m, 2H), 2.45-2.53 (m, 1H), 2.38-2.45 (m, 1H), 1.64-1.75 (m, 2H), 1.50 (s, 9H), 1.35-1.46 (m, 1H), 1.15-1.25 (m, 1H); MS (ESI+) m/z 594 (M+H)+, 611 (M+NH4)+.

Sources & evidence

ORD record
ord-517fcc51936f45eba7353ffb3d3368ac
Source dataset
uspto-grants-2014_04
Patent number
US08691865B2

Reaction notes

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