Hydrogen Peroxide → HCID 86705568, compound

HRID 2279586Notes

Reaction equation

HRID 2279586 reaction equation
[Li+].[OH-:2].OO.[CH2:5]([N:12]1[CH2:16][C@@H:15]([C:17]2[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[C:19]([F:27])[CH:18]=2)[C@H:14]([C:28](N2[C@H](C3C=CC=CC=3)COC2=O)=[O:29])[CH2:13]1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.S([O-])([O-])=O.[Na+].[Na+].OS([O-])(=O)=O.[K+]>C1COCC1>[CH2:5]([N:12]1[CH2:16][C@@H:15]([C:17]2[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:24])[F:25])=[C:19]([F:27])[CH:18]=2)[C@H:14]([C:28]([OH:29])=[O:2])[CH2:13]1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

7

Reactant 5

HCID 784Hydrogen PeroxideHCID 3939Lithium HydroxideHCID 24437Sodium SulfiteHCID 516920Potassium bisulfateHCID 86705566HCID 86705566, compound

Product 1

HCID 86705568HCID 86705568, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a 1M LiOH solution (8.20 mL, 8.20 mmol) cooled to 0° C. was added 30% hydrogen peroxide (1.06 mL, 10.2 mmol). The mixture was stirred for 10 min at 0° C. and then added to solution of 340 (2.10 g, 4.10 mmol) in THF (15 mL) cooled to 0° C. over 15 min. The mixture was stirred for 4 h at 0° C. then 2M sodium sulfite (10 mL) was added and the mixture stirred for 30 min. The pH was adjusted to ca. 5-6 with 2M KHSO4 and the mixture was thrice extracted with 50 mL portions of 3:1 CHCl3/IPA. The combined organic extracts were combined, washed with brine, dried (MgSO4), filtered and evaporated. The crude product was purified by SiO2 chromatography eluting with a MeOH/DCM gradient (5 to 10% MeOH) to afford 1.28 g (85.0%) of (3S,4R)-1-benzyl-4-(3-fluoro-4-(trifluoromethyl)phenyl)pyrrolidine-3-carboxylic acid (342) as white solid: MS m/z (APCI-neg) M−1=366.

Workup

  1. temperaturecooled to 0° C. over 15 min
  2. stirringThe mixture was stirred for 4 h at 0° C.
  3. stirringthe mixture stirred for 30 min
  4. extractionextracted with 50 mL portions of 3:1 CHCl3/IPA
  5. washwashed with brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customevaporated
  9. customThe crude product was purified by SiO2 chromatography
  10. washeluting with a MeOH/DCM gradient (5 to 10% MeOH)

Sources & evidence

ORD record
ord-55f1353084ed4f9eb082ce0135ae52f7
Source dataset
uspto-grants-2015_09
Patent number
US09133187B2

Reaction notes

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