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

HRID 594529Notes

Reaction equation

HRID 594529 reaction equation
[NH2:1][CH:2]([C:9]1[C:14]([O:15][CH3:16])=[CH:13][CH:12]=[CH:11][C:10]=1[O:17][CH3:18])[CH2:3][CH2:4][C:5]([O:7]C)=O.[CH:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=[CH:21][C:20]=1[CH:29]=O>>[CH3:18][O:17][C:10]1[CH:11]=[CH:12][CH:13]=[C:14]([O:15][CH3:16])[C:9]=1[CH:2]1[N:1]([CH2:29][C:20]2[CH:21]=[CH:22][C:23]3[C:28](=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH:19]=2)[C:5](=[O:7])[CH2:4][CH2:3]1

Participants

3

Reactant 2

HCID 62012-NaphthalenecarboxaldehydeHCID 69082397Methyl 4-amino-4-(2,6-dimethoxyphenyl)butanoate

Product 1

HCID 690809855-(2,6-Dimethoxyphenyl)-1-(naphthalen-2-ylmethyl)pyrrolidin-2-one

Procedure

Prepared according to the described general procedure 1 (GP1) by reaction of methyl 4-amino-4-(2,6-dimethoxyphenyl)butanoate with commercially available 2-naphthaldehyde. Subsequent purification by preparative HPLC afforded the target compound. LC-MS (conditions A): tR=0.87 min.; [M+H]+: 362.35 g/mol.

Workup

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

Sources & evidence

ORD record
ord-d64a509b9b0f4340984d3456ad28f705
Source dataset
uspto-grants-2016_01
Patent number
US09242970B2

Reaction notes

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