Sodium Hydroxide → (R)-tert-butyl 2-(3-fluorophenyl)-4-oxopyrrolidine-1-carboxylate

HRID 63986Notes

Reaction equation

HRID 63986 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C@H:8]2[CH2:12][C@@H:11]([OH:13])[CH2:10][N:9]2[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH:5]=[CH:6][CH:7]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[OH-].[Na+]>C(Cl)Cl.[Cl-].[Na+].O>[F:1][C:2]1[CH:3]=[C:4]([C@H:8]2[CH2:12][C:11](=[O:13])[CH2:10][N:9]2[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 159087TriacetoxyperiodinaneHCID 66685055(2R,4R)-tert-butyl 2-(3-fluorophenyl)-4-hydroxypyrrolidine-1-carboxylate

Product 1

HCID 66684965(R)-tert-butyl 2-(3-fluorophenyl)-4-oxopyrrolidine-1-carboxylateYield 43.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

(2R,4R)-tert-Butyl 2-(3-fluorophenyl)-4-hydroxypyrrolidine-1-carboxylate (1.4 g, 4.98 mmol) and Dess-Martin periodinane (2.53 g, 5.97 mmol) were mixed in 50 mL DCM and stirred at ambient temperature overnight. For workup, 20 mL 1N NaOH was added to reaction, and stirred for 30 minutes, followed by addition of 20 mL brine. The reaction mixture was extracted with several portions of DCM. The combined organic extracts were filtered through a Phase Separator filter paper, concentrated, and purified by reverse phase chromatography, eluting with 20-70% acetonitrile/water to yield the product as yellow oil (600 mg, 43% yield.)

Workup

  1. stirringstirred for 30 minutes
  2. extractionThe reaction mixture was extracted with several portions of DCM
  3. filtrationThe combined organic extracts were filtered through a Phase Separator
  4. filtrationfilter paper
  5. concentrationconcentrated
  6. custompurified by reverse phase chromatography
  7. washeluting with 20-70% acetonitrile/water

Sources & evidence

ORD record
ord-e0767068dcc34f30ac5fa21029e8010f
Source dataset
uspto-grants-2016_09
Patent number
US09447104B2

Reaction notes

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