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Water → HCID 67399360, compound

HRID 70653
Notes
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Reaction equation

HRID 70653 reaction equation
[BH4-].[Na+].[C:3]([C:6]1[CH:7]=[CH:8][C:9](/[C:14](/[C:33]2[CH:38]=[CH:37][C:36]([C:39]([CH3:42])([CH3:41])[CH3:40])=[CH:35][CH:34]=2)=[CH:15]/[C@@H:16]2[N:20]([CH2:21][C:22]3[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][C:23]=3[O:30][CH3:31])[C:19](=[O:32])[CH2:18][CH2:17]2)=[N:10][C:11]=1[O:12][CH3:13])(=[O:5])[CH3:4].O>CO>[C:39]([C:36]1[CH:37]=[CH:38][C:33](/[C:14](/[C:9]2[CH:8]=[CH:7][C:6]([CH:3]([OH:5])[CH3:4])=[C:11]([O:12][CH3:13])[N:10]=2)=[CH:15]\[C@@H:16]2[N:20]([CH2:21][C:22]3[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][C:23]=3[O:30][CH3:31])[C:19](=[O:32])[CH2:18][CH2:17]2)=[CH:34][CH:35]=1)([CH3:40])([CH3:41])[CH3:42]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 67400682(5R)-5-[(E)-2-(5-acetyl-6-methoxypyridin-2-yl)-2-(4-tert-butylphenyl)ethenyl]-1-(2,4-dimethoxybenzyl)pyrrolidin-2-one

Product 1

HCID 67399360HCID 67399360, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (108 mg) was added to a solution of (5R)-5-[(E)-2-(5-acetyl-6-methoxypyridin-2-yl)-2-(4-tert-butylphenyl)ethenyl]-1-(2,4-dimethoxybenzyl)pyrrolidin-2-one obtained in Example 4-175(1) (773 mg) in methanol under ice-cooling, followed by stirring for 40 minutes. The reaction solution was poured into water and extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate. After filtration, the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:0→1:1) to give (5R)-5-{(E)-2-(4-tert-butylphenyl)-2-[5-(1-hydroxyethyl)-6-methoxypyridin-2-yl]ethenyl}-1-(2,4-dimethoxybenzyl)pyrrolidin-2-one as a colorless amorphous (388 mg).

Workup

  1. temperaturecooling
  2. extractionextracted with chloroform
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationAfter filtration
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:0→1:1)

Sources & evidence

ORD record
ord-25f016a7e14a4bbb9de5a243f40163dc
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08822503B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes