2-Ethoxy-6-fluorobenzaldehyde → rac-(3S*,5S*)-3-chloro-1-(3-chloro-4-(trifluoromethoxy)benzyl)-5-(2-ethoxy-6-fluorophenyl)pyrrolidin-2-one

HRID 594761Notes

Reaction equation

HRID 594761 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:13][NH2:14])[CH:5]=[CH:6][C:7]=1[O:8][C:9]([F:12])([F:11])[F:10].[CH2:15]([O:17][C:18]1[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[C:19]=1[CH:20]=O)[CH3:16]>>[Cl:1][CH:2]1[CH2:3][CH:20]([C:19]2[C:22]([F:26])=[CH:23][CH:24]=[CH:25][C:18]=2[O:17][CH2:15][CH3:16])[N:14]([CH2:13][C:4]2[CH:5]=[CH:6][C:7]([O:8][C:9]([F:11])([F:12])[F:10])=[C:2]([Cl:1])[CH:3]=2)[C:7]1=[O:8]

Participants

3

Reactant 2

HCID 38158942-Ethoxy-6-fluorobenzaldehydeHCID 534144551-[3-Chloro-4-(trifluoromethoxy)phenyl]methanamine

Product 1

HCID 86695670rac-(3S*,5S*)-3-chloro-1-(3-chloro-4-(trifluoromethoxy)benzyl)-5-(2-ethoxy-6-fluorophenyl)pyrrolidin-2-one

Procedure

Prepared according to the described general procedures 10A2 (GP10A2), 10B (GP10B), 10F (GP10F), and 10D (GP10D) using commercially available (3-chloro-4-(trifluoromethoxy)phenyl)methanamine and synthesized 2-ethoxy-6-fluorobenzaldehyde. Subsequent purification by preparative HPLC afforded the target compound. LC-MS (conditions A): tR=1.00 min.; [M+H]+: 465.77 g/mol.

Workup

  1. customPrepared
  2. customSubsequent purification by preparative HPLC
  3. customafforded the target compound

Sources & evidence

ORD record
ord-50ef022031fc49bfb72294809a6ebcb8
Source dataset
uspto-grants-2016_01
Patent number
US09242970B2

Reaction notes

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