Diethyl Ether → (3r)-1-(4-Nitrophenyl)pyrrolidin-3-amine trifluoroacetate salt

HRID 1441365Notes

Reaction equation

HRID 1441365 reaction equation
C(OC(=O)[NH:7][C@@H:8]1[CH2:12][CH2:11][N:10]([C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=2)[CH2:9]1)(C)(C)C.[C:23]([OH:29])([C:25]([F:28])([F:27])[F:26])=[O:24].CCOCC>C(Cl)Cl>[F:26][C:25]([F:28])([F:27])[C:23]([OH:29])=[O:24].[N+:19]([C:16]1[CH:17]=[CH:18][C:13]([N:10]2[CH2:11][CH2:12][C@@H:8]([NH2:7])[CH2:9]2)=[CH:14][CH:15]=1)([O-:21])=[O:20]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 6422Trifluoroacetic acidHCID 86594863tert-butyl [(3R)-1-(4-nitrophenyl)pyrrolidin-3-yl]carbamate

Product 1

HCID 68688649(3r)-1-(4-Nitrophenyl)pyrrolidin-3-amine trifluoroacetate saltYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl[(3R)-1-(4-nitrophenyl)pyrrolidin-3-yl]carbamate (Method 40; 1.0 g, 3.26 mmol) in DCM (15 ml) was reacted with TFA (7.5 ml) at room temperature for 18 hours. Pouring into cold ether (200 ml) gave on filtration the title compound (0.97 g, 93%). NMR: 2.03-2.17 (m, 1H), 2.22-2.44 (m, 1H), 3.40-3.60 (m, 3H), 3.68-3.74 (m, 1H), 3.95-4.08 (m, 1H), 6.66 (d, 2H), 8.08 (d, 2H), 8.14 (s, 2H).

Sources & evidence

ORD record
ord-3b2b9258dc5a4965a52d09fcbca602e2
Source dataset
uspto-grants-2010_02
Patent number
US07655652B2

Reaction notes

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