2-Naphthalenecarboxaldehyde → 5-(2,6-Dimethoxyphenyl)-3-methyl-1-(naphthalen-2-ylmethyl)pyrrolidin-2-one

HRID 594549Notes

Reaction equation

HRID 594549 reaction equation
[NH2:1][CH:2]([C:11]1[C:16]([O:17][CH3:18])=[CH:15][CH:14]=[CH:13][C:12]=1[O:19][CH3:20])[CH2:3][CH:4]([CH3:10])[C:5]([O:7]CC)=O.[CH:21]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=[CH:23][C:22]=1[CH:31]=O>>[CH3:18][O:17][C:16]1[CH:15]=[CH:14][CH:13]=[C:12]([O:19][CH3:20])[C:11]=1[CH:2]1[N:1]([CH2:31][C:22]2[CH:23]=[CH:24][C:25]3[C:30](=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH:21]=2)[C:5](=[O:7])[CH:4]([CH3:10])[CH2:3]1

Participants

3

Reactant 2

HCID 62012-NaphthalenecarboxaldehydeHCID 69085588Ethyl 4-amino-4-(2,6-dimethoxyphenyl)-2-methylbutanoate

Product 1

HCID 690836365-(2,6-Dimethoxyphenyl)-3-methyl-1-(naphthalen-2-ylmethyl)pyrrolidin-2-one

Procedure

Prepared according to the described general procedure 2 (GP2) by reaction of ethyl 4-amino-4-(2,6-dimethoxyphenyl)-2-methylbutanoate with commercially available 2-naphthaldehyde. Subsequent purification by preparative HPLC afforded the target compound. LC-MS (conditions A): tR=0.92 min.; [M+H]+: 376.02 g/mol.

Workup

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

Sources & evidence

ORD record
ord-91a6619587174d3f89698cd5c17482d8
Source dataset
uspto-grants-2016_01
Patent number
US09242970B2

Reaction notes

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