Dibenzo(b,d)furan-2-carboxaldehyde → 1-(Dibenzo[b,d]furan-2-ylmethyl)-5-(2-fluoro-6-methoxyphenyl)-3-methylpyrrolidin-2-one

HRID 594696Notes

Reaction equation

HRID 594696 reaction equation
[NH2:1][CH:2]([C:11]1[C:16]([O:17][CH3:18])=[CH:15][CH:14]=[CH:13][C:12]=1[F:19])[CH2:3][CH:4]([CH3:10])[C:5]([O:7]CC)=O.[CH:20]1[C:28]2[C:27]3[CH:29]=[CH:30][CH:31]=[CH:32][C:26]=3[O:25][C:24]=2[CH:23]=[CH:22][C:21]=1[CH:33]=O>>[CH:20]1[C:28]2[C:27]3[CH:29]=[CH:30][CH:31]=[CH:32][C:26]=3[O:25][C:24]=2[CH:23]=[CH:22][C:21]=1[CH2:33][N:1]1[CH:2]([C:11]2[C:16]([O:17][CH3:18])=[CH:15][CH:14]=[CH:13][C:12]=2[F:19])[CH2:3][CH:4]([CH3:10])[C:5]1=[O:7]

Participants

3

Reactant 2

HCID 220843Dibenzo(b,d)furan-2-carboxaldehydeHCID 69085707Ethyl 4-amino-4-(2-fluoro-6-methoxyphenyl)-2-methylbutanoate

Product 1

HCID 866956581-(Dibenzo[b,d]furan-2-ylmethyl)-5-(2-fluoro-6-methoxyphenyl)-3-methylpyrrolidin-2-one

Procedure

Prepared according to the described general procedure 2 (GP2) by reaction of ethyl 4-amino-4-(2-fluoro-6-methoxyphenyl)-2-methylbutanoate with commercially available dibenzo[b,d]furan-2-carbaldehyde. Subsequent purification by preparative HPLC afforded the target compound. LC-MS (conditions A): tR=0.96 min.; [M+H]+: 403.87 g/mol.

Workup

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

Sources & evidence

ORD record
ord-b7dffb44654b482cb8910c3ec20615d3
Source dataset
uspto-grants-2016_01
Patent number
US09242970B2

Reaction notes

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