Trichloroisocyanuric Acid → HCID 118590542, compound

HRID 1054460Notes

Reaction equation

HRID 1054460 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:21][CH:22]2[CH2:26][CH2:25][O:24][CH2:23]2)=[C:6]([C@H:8]2[CH2:12][CH:11]([OH:13])[CH2:10][N:9]2[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH:7]=1.ClN1C(=O)N(Cl)C(=O)N(Cl)C1=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[C:17]([O:16][C:14]([N:9]1[CH2:10][C:11](=[O:13])[CH2:12][C@@H:8]1[C:6]1[CH:7]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=1[O:21][CH:22]1[CH2:26][CH2:25][O:24][CH2:23]1)=[O:15])([CH3:20])([CH3:18])[CH3:19]

Participants

5

Reactant 3

HCID 6909Trichloroisocyanuric AcidHCID 516892Sodium BicarbonateHCID 118590359HCID 118590359, compound

Product 1

HCID 118590542HCID 118590542, compoundYield 97.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2R)-tert-butyl 2-(5-fluoro-2-((tetrahydrofuran-3-yl)oxy)phenyl)-4-hydroxypyrrolidine-1-carboxylate (18.0 g, 49 mmol) in DCM (150 mL) at −40° C. was added trichloroisocyanuric acid (12.5 g, 54 mmol) followed by 2,2,6,6-tetramethylpiperidino-1-oxy (TEMPO) (0.76 g, 4.9 mmol). After stirring 1 h at −40° C. to −10° C., the reaction mixture was poured into cold saturated aqueous NaHCO3 solution (200 ml), extracted with DCM (400 ml), combined extracts were washed with water and brine solution, dried over anhydrous sodium sulfate and concentrated to dryness to give the corresponding ketone (17.5 g, crude yield 98%) as pale yellow oil, which was used without purification in the next step. MS (ESI): m/z 266.2 (de-Boc), (M+H).

Workup

  1. extractionextracted with DCM (400 ml)
  2. washwere washed with water and brine solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-05024a8b3f834bf2b23ab2feb5439c15
Source dataset
uspto-grants-2016_07
Patent number
US09394305B2

Reaction notes

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