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1,10-Phenanthroline → tert-Butyl (2R)-2-(1,3-benzoxazol-2-yl)pyrrolidine-1-carboxylate

HRID 633902
Notes
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Reaction equation

HRID 633902 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]([C@H:11]1[CH2:15][CH2:14][CH2:13][N:12]1[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[O:10].C([O-])([O-])=O.[Cs+].[Cs+].N1C2C(=CC=C3C=2N=CC=C3)C=CC=1>COCCOC.[Cu]I>[O:10]1[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[N:8]=[C:9]1[C@H:11]1[CH2:15][CH2:14][CH2:13][N:12]1[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 13181,10-PhenanthrolineHCID 10796Cesium carbonateHCID 68338101tert-Butyl (2R)-2-{[(2-bromophenyl)amino]carbonyl}pyrrolidine-1-carboxylate

Product 1

HCID 68338089tert-Butyl (2R)-2-(1,3-benzoxazol-2-yl)pyrrolidine-1-carboxylateYield 58%

Reagents, catalysts & solvents 2

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
Catalyst
HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
85 °C

Procedure

In a 25 mL flask, tert-butyl(2R)-2-{[(2-bromophenyl)amino]carbonyl}pyrrolidine-1-carboxylate (194 mg, 0.53 mmol; which may be prepared as described in Step 1) was dissolved in DME (4 mL) under nitrogen at room temperature. CuI (6 mg, 0.03 mmol), Cs2CO3 (261 mg, 0.80 mmol) and 1,10-phenanthroline (26 mg, 0.14 mmol) were added then the reaction mixture was heated at 85° C. for 24 h. The mixture was cooled to room temperature and concentrated to dryness. The residue was dissolved in dichloromethane and filtered on Celite to eliminate the copper residue. The filtrate was concentrated and the residue purified on preparative TLC (Pentane/EtOAc, 85/15 to 50/50) to give the title compound (88 mg, 58%) as a solid.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. concentrationconcentrated to dryness
  3. dissolutionThe residue was dissolved in dichloromethane
  4. filtrationfiltered on Celite
  5. concentrationThe filtrate was concentrated
  6. customthe residue purified on preparative TLC (Pentane/EtOAc, 85/15 to 50/50)

Sources & evidence

ORD record
ord-02b5e97e5377447eb677598ecaea9865
Source dataset
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09321769B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes