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

HRID 1092607Notes

Reaction equation

HRID 1092607 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[C:13]([OH:15])=O)=[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)C1C=C(S(N2C[C@H]3[C@H](N)CC[C@H]3C2)(=O)=O)C=CC=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][CH2:10][CH2:11][CH2:12][N:8]4[C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])=[O:15])[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 66590317tert-butyl(2S)-2-{[((3aR,4S,6aS)-2-{[3-(trifluoromethyl)phenyl]sulfonyl}octahydrocyclopenta[c]pyrrol-4-yl)amino]carbonyl}piperidine-1-carboxylate

Procedure

The title compound was prepared by substituting (S)-1-(tert-butoxycarbonyl)piperidine-2-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 252D 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) δ ppm 8.37-8.38 (bs, 1H), 8.32 (d, J=5.2 Hz, 1H), 8.19 (d, J=7.9 Hz, 1H), 7.91 (d, J=7.9 Hz, 1H), 7.71 (t, J=7.8 Hz, 1H), 4.07-4.23 (m, 2H), 3.84 (dd, J=9.9, 2.2 Hz, 1H), 3.46 (td, J=12.9, 2.8 Hz, 1H), 3.16 (d, J=9.2 Hz, 1H), 3.12 (dd, J=9.5, 7.6 Hz, 1H), 2.90-2.94 (m, 1H), 2.41-2.57 (bs, 2H), 2.24-2.29 (m, 1H), 1.75-1.97 (m, 2H), 1.53-1.65 (m, 3H), 1.49-1.55 (m, 2H), 1.48 (s, 9H), 1.42-1.51 (m, 1H), 1.29-1.39 (m, 1H), 1.17-1.29 (m, 1H); MS (ESI+) m/z 563 (M+H)+.

Sources & evidence

ORD record
ord-ddf03465ed02431197b7438a2e7a5dd6
Source dataset
uspto-grants-2012_03
Patent number
US08129417B2

Reaction notes

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