Diisopropylethylamine → HCID 178513419, compound

HRID 273179Notes

Reaction equation

HRID 273179 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][CH:23]=1)[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]2[C:17](=[O:18])[CH2:16][C@@H:15]([C:19]#[N:20])[CH2:14]2)=[CH:9][CH:8]=1.Cl.[NH2:25][OH:26].C(N(CC)C(C)C)(C)C>C(O)C>[F:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][CH:23]=1)[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]2[C:17](=[O:18])[CH2:16][C@@H:15]([C:19]([NH:25][OH:26])=[NH:20])[CH2:14]2)=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 443297Hydroxyamine hydrochlorideHCID 69309400(R)-1-[4-(3-Fluoro-benzyloxy)-phenyl]-5-oxo-pyrrolidine-3-carbonitrile

Product 1

HCID 178513419HCID 178513419, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(R)-1-[4-(3-Fluoro-benzyloxy)-phenyl]-5-oxo-pyrrolidine-3-carbonitrile (0.211 g, 0.001 mol) and hydroxylamine hydrochloride (0.047 g, 0.001 mol) were dissolved in ethanol (4 ml) and N,N-diisopropylethylamine (0.120 ml, 0.001 mol) was added. The reaction mixture was stirred under reflux for three hours. The reaction was cooled to room temperature, the solvent was evaporated and the residue extracted with dichloromethane and purified by column chromatography on silica gel using a 19:1-mixture of dichloromethane and methanol as the eluent to yield (0.220 g, 94% of theory) of a yellow oil. MS (m/e)=344.3(M+H)+.

Workup

  1. temperatureunder reflux for three hours
  2. customthe solvent was evaporated
  3. extractionthe residue extracted with dichloromethane
  4. custompurified by column chromatography on silica gel using a 19
  5. custom1-mixture of dichloromethane and methanol as the eluent to yield (0.220 g, 94% of theory) of a yellow oil

Sources & evidence

ORD record
ord-46b255942eab44d7811461e575d1c3b7
Source dataset
uspto-grants-2008_11
Patent number
US07456210B2

Reaction notes

Loading…