Pivalaldehyde → HCID 66590492, compound

HRID 2363615Notes

Reaction equation

HRID 2363615 reaction equation
FC(F)(F)C1C=C(S([N:12]2[CH2:16][C@H:15]3[C@H:17]([NH2:20])[CH2:18][CH2:19][C@H:14]3[CH2:13]2)(=O)=O)C=CC=1.[CH:23](=O)[C:24]([CH3:27])(C)[CH3:25]>CC(C)=O>[CH2:25]([N:12]1[CH2:16][C@@H:15]2[C@@H:17]([NH:20][CH:18]([CH3:19])[CH3:17])[CH2:18][CH2:19][C@@H:14]2[CH2:13]1)[C:24]1[CH:27]=[CH:15][CH:14]=[CH:13][CH:23]=1

Participants

4

Reactant 2

HCID 12417PivalaldehydeHCID 66590613(3aS,4R,6aR)-2-(3-(Trifluoromethyl)phenylsulfonyl)octahydrocyclopenta[c]pyrrol-4-amine

Product 1

HCID 66590492HCID 66590492, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

(3aR,4S,6aS)-2-Benzyl-N-isopropyloctahydrocyclopenta[c]pyrrol-4-amine was prepared by substituting (3aR,4S,6aS)-2-benzyloctahydrocyclopenta[c]pyrrol-4-amine from Example 33 Step A for (3aS,4R,6aR)-2-(3-(trifluoromethyl)phenylsulfonyl)octahydrocyclopenta[c]pyrrol-4-amine and acetone for pivalaldehyde in the procedure described in Example 281: 1H NMR (500 MHz, pyridine-d5) δ ppm 7.48 (d, J=7.5, 2H), 7.39 (t, J=7.5, 2H), 7.29 (t, J=7.3, 1H), 3.61-3.51 (m, 2H), 3.05 (dd, J=12.1, 5.4, 1H), 2.87-2.78 (m, 1H), 2.61-2.51 (m, 2H), 2.43-2.36 (m, 2H), 2.35-2.30 (m, 1H), 2.28-2.21 (m, 1H), 2.00-1.93 (m, 1H), 1.93-1.87 (m, 1H), 1.42-1.28 (m, 3H), 1.05-0.98 (m, 6H); MS (ESI+) m/z 259 (M+H)+.

Sources & evidence

ORD record
ord-5baa52c9653f44d7a0b1b5f17bbf7071
Source dataset
uspto-grants-2014_04
Patent number
US08691865B2

Reaction notes

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