3-(Trifluoromethyl)benzenesulfonyl chloride → HCID 66590601, compound

HRID 2363573Notes

Reaction equation

HRID 2363573 reaction equation
C([N:8]1[CH2:12][C@@H:11]2[C@@H:13]([NH2:16])[CH2:14][CH2:15][C@@H:10]2[CH2:9]1)C1C=CC=CC=1.[F:17][C:18]([F:30])([F:29])[C:19]1[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1.FC(F)(F)C1C=C(S(Cl)(=O)=O)C=CC=1>>[F:30][C:18]([F:17])([F:29])[C:19]1[CH:20]=[CH:21][C:22]([S:25]([N:8]2[CH2:12][C@H:11]3[C@H:13]([NH2:16])[CH2:14][CH2:15][C@H:10]3[CH2:9]2)(=[O:27])=[O:26])=[CH:23][CH:24]=1

Participants

4

Reactant 3

HCID 27332503-(Trifluoromethyl)benzenesulfonyl chlorideHCID 27773994-(Trifluoromethyl)benzenesulfonyl chlorideHCID 66591011(3aR,4S,6aS)-2-benzyloctahydrocyclopenta[c]pyrrol-4-amine

Product 1

HCID 66590601HCID 66590601, compound

Procedure

(3aS,4R,6aR)-2-(4-(Trifluoromethyl)phenylsulfonyl)octahydrocyclopenta[c]pyrrol-4-amine was prepared by following the procedures described in Example 252 Steps A-D substituting (3aS,4R,6aR)-2-benzyloctahydrocyclopenta[c]pyrrol-4-amine from Step E of Example 16 for (3aR,4S,6aS)-2-benzyloctahydrocyclopenta[c]pyrrol-4-amine in Step A of Example 252 and 4-(trifluoromethyl)benzene-1-sulfonyl chloride for 3-(trifluoromethyl)benzene-1-sulfonyl chloride in the procedure described in Step C of Example 252: 1H NMR (500 MHz, pyridine-d5) δ ppm 8.15 (d, J=8.2, 2H), 7.92 (d, J=8.3, 2H), 3.40 (dd, J=9.8, 2.9, 1H), 3.13 (dd, J=9.7, 3.2, 1H), 3.06-2.93 (m, 3H), 2.54 (s, 1H), 2.21-2.12 (m, 1H), 1.93-1.85 (m, 1H), 1.78-1.69 (m, 1H), 1.67-1.33 (m, 2H), 1.33-1.15 (m, 2H); MS (ESI+) m/z 335 (M+H)+.

Sources & evidence

ORD record
ord-3f1c5cb1b2904efc9f29163b075b5ed3
Source dataset
uspto-grants-2014_04
Patent number
US08691865B2

Reaction notes

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