1-Piperazinecarboxylic acid, ethyl ester → 4-[(2S,4S)-1-Benzyl-4-(3,5-bis-trifluoromethyl-benzylamino)-pyrrolidine-2-carbonyl]-piperazine-1-carboxylic acid ethyl ester

HRID 490634Notes

Reaction equation

HRID 490634 reaction equation
[CH2:1]([N:8]1[CH2:12][CH:11]([NH:13][CH2:14][C:15]2[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[C:17]([C:25]([F:28])([F:27])[F:26])[CH:16]=2)[CH2:10][CH:9]1[C:29](O)=[O:30])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:32]([O:34][C:35]([N:37]1[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]1)=[O:36])[CH3:33]>>[CH2:32]([O:34][C:35]([N:37]1[CH2:38][CH2:39][N:40]([C:29]([C@@H:9]2[CH2:10][C@H:11]([NH:13][CH2:14][C:15]3[CH:20]=[C:19]([C:21]([F:23])([F:24])[F:22])[CH:18]=[C:17]([C:25]([F:28])([F:27])[F:26])[CH:16]=3)[CH2:12][N:8]2[CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[O:30])[CH2:41][CH2:42]1)=[O:36])[CH3:33]

Participants

3

Reactant 2

HCID 84311-Piperazinecarboxylic acid, ethyl esterHCID 866253011-Benzyl-4-(3,5-bis-trifluoromethyl-benzylamino)-pyrrolidine-2-carboxylic acid

Product 1

HCID 866253044-[(2S,4S)-1-Benzyl-4-(3,5-bis-trifluoromethyl-benzylamino)-pyrrolidine-2-carbonyl]-piperazine-1-carboxylic acid ethyl esterYield 7.5%

Procedure

As described for Example 56d, 1-benzyl-4-(3,5-bis-trifluoromethyl-benzylamino)-pyrrolidine-2-carboxylic acid (65 mg, 0.146 mmol) was converted, using piperazine-1-carboxylic acid ethyl ester instead of 1-(3-trifluoromethyl-phenyl)-piperazine, to the title compound (6.8 mg, 7.5%) as light yellow oil. MS m/e=587.3 [M+H]+.

Sources & evidence

ORD record
ord-4b477f8ea26b4172bc8be83426e421b5
Source dataset
uspto-grants-2009_05
Patent number
US07528136B2

Reaction notes

Loading…