Sodium Carbonate → 3-(Trifluoromethyl)benzyl 4-hydroxy-1-(3-(trifluoromethyl)benzyl)pyrrolidine-2-carboxylate

HRID 712835

Reaction equation

HRID 712835 reaction equation
[OH:1][C@H:2]1[CH2:6][NH:5][C@@H:4]([C:7]([OH:9])=[O:8])[CH2:3]1.[F:10][C:11]([F:21])([F:20])[C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=1)[CH2:15]Br.C([O-])([O-])=O.[Na+].[Na+]>>[OH:1][CH:2]1[CH2:6][N:5]([CH2:15][C:14]2[CH:17]=[CH:18][CH:19]=[C:12]([C:11]([F:21])([F:20])[F:10])[CH:13]=2)[CH:4]([C:7]([O:9][CH2:15][C:14]2[CH:17]=[CH:18][CH:19]=[C:12]([C:11]([F:10])([F:20])[F:21])[CH:13]=2)=[O:8])[CH2:3]1

Participants

4

Reactant 3

HCID 10340Sodium CarbonateHCID 1230611-(Bromomethyl)-3-(trifluoromethyl)benzeneHCID 440014Cis-4-Hydroxy-D-Proline

Product 1

HCID 903538573-(Trifluoromethyl)benzyl 4-hydroxy-1-(3-(trifluoromethyl)benzyl)pyrrolidine-2-carboxylate

Procedure

The title compound (D81) (1.02 g) was prepared according to the general procedure for substituted benzyl amines preparation starting from cis-4-Hydroxy-D-proline (4.0 g; available from Aldrich#H5877) and 3-(Trifluoromethyl)benzyl bromide (9.37 ml). (Na2CO3: 2.5 eq; Reaction time: 24 hrs; 60° C.).

Sources & evidence

ORD record
ord-47c1ce7c4c6d4ae78b39c83b454689b6
Source dataset
uspto-grants-2015_11
Patent number
US09181279B2

Linked notes

Loading…