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Sodium Carbonate → 5-[4-Biphenyl-3-yl-3-(tert-butyl-dimethyl-silanyloxy)-butyl]-pyrrolidin-2-one

HRID 1267442
Notes
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Reaction equation

HRID 1267442 reaction equation
Br[C:2]([O:12][Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14])([CH3:11])[CH2:3][CH2:4][CH:5]1[NH:9][C:8](=[O:10])[CH2:7][CH2:6]1.[C:20]1(B(O)O)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>[C:20]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:25]=[CH:24][CH:23]=[C:22]([CH2:11][CH:2]([O:12][Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14])[CH2:3][CH2:4][CH:5]2[NH:9][C:8](=[O:10])[CH2:7][CH2:6]2)[CH:21]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 227124675-[3-Bromo-3-(tert-butyl-dimethyl-silanyloxy)-butyl]-pyrrolidin-2-one

Product 1

HCID 227124795-[4-Biphenyl-3-yl-3-(tert-butyl-dimethyl-silanyloxy)-butyl]-pyrrolidin-2-oneYield 175.4%

Reagents, catalysts & solvents 4

HCID 80271
Tri-o-tolylphosphine
Catalyst
HCID 167845palladium(II) acetateCatalyst
HCID 962WaterSolvent
HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of 5-[3-bromo-3-(tert-butyl-dimethyl-silanyloxy)-butyl]-pyrrolidin-2-one (750 mg, 1.76 mmol) in DME (15 mL) was added phenylboronic acid (236 mg, 1.93 mmol). Palladium acetate (26.8 mg, 0.120 mmol) and tri-o-tolylphosphine (39.5 mg, 0.130 mmol) were added, followed by a solution of Na2CO3 (373 mg, 3.52 mmol) in water (1.8 mL). The reaction mixture was heated under reflux for 24 h. The reaction mixture was cooled and the volatiles were removed in vacuo. The residue was diluted with brine and EtOAc. The aqueous solution was washed with EtOAc (3×) and the combined organic extracts were dried (MgSO4), filtered and concentrated. Purification by medium pressure chromatography eluting with a solvent gradient (1:1 hexanes:EtOAc to EtOAc to 1% MeOH in CH2Cl2 to 3% MeOH in CH2Cl2 to 5% MeOH in CH2Cl2) provided 5-[4-biphenyl-3-yl-3-(tert-butyl-dimethyl-silanyloxy)-butyl]-pyrrolidin-2-one (717.3 mg). 1H NMR (CDCl3) δ7.57 (m, 2H), 7.43 (m, 2H), 7.33 (m, 3H), 7.11 (m, 2H), 5.78 (m, 1H), 3.91 (m, 1H), 3.59 (m, 1H), 2.76 (m, 2H), 2.27 (m, 3H), 1.73-1.38 (m, 5H), 0.83 (s, 9H), −0.03 (d, 3H), −0.16 (d, 3H); MS 424.3 (M+1).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 24 h
  3. temperatureThe reaction mixture was cooled
  4. customthe volatiles were removed in vacuo
  5. additionThe residue was diluted with brine and EtOAc
  6. washThe aqueous solution was washed with EtOAc (3×)
  7. dry with materialthe combined organic extracts were dried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customPurification by medium pressure chromatography
  11. washeluting with a solvent gradient (1:1 hexanes:EtOAc to EtOAc to 1% MeOH in CH2Cl2 to 3% MeOH in CH2Cl2 to 5% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-c3d18ff3d83745a28405e81cf47e4a59
Source dataset
uspto-grants-2003_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06552067B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes