Trifluoroacetic acid → HCID 66982187, compound

HRID 712805Notes

Reaction equation

HRID 712805 reaction equation
[Si:1]([O:18][CH2:19][C@@H:20]1[N:24]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[C:23](=O)[CH:22]([CH2:33][Sn](C)(C)C)[CH2:21]1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O.C([O-])([O-])=O.[K+].[K+]>C1COCC1.C(Cl)Cl>[Si:1]([O:18][CH2:19][CH:20]1[CH2:21][CH:22]2[CH:23]([CH2:33]2)[N:24]1[C:25]([O:27][C:28]([CH3:30])([CH3:29])[CH3:31])=[O:26])([C:14]([CH3:15])([CH3:17])[CH3:16])([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 131733991HCID 131733991, compound

Product 1

HCID 66982187HCID 66982187, compoundYield 67.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of (5R)-tert-butyl 5-(((tert-butyldiphenylsilyl)oxy)methyl)-2-oxo-3-((trimethylstannyl)methyl)pyrrolidine-1-carboxylate (D30) (3.1 g, 6.86 mmol) in THF (200 ml) cooled at −78° C., LiEt3BH 1M sol in THF (17.2 ml) was added dropwise. The reaction was left at −78° C. for 2 hrs then water (50 ml) and the reaction extracted with Et2O (3×100 ml). The organic phases were combined, dried over Na2SO4 and evaporated in vacuo to afford a residue which was dissolved in DCM (120 ml) and cooled at 0° C. TFA (1.31 ml, 17.2 mmol) was added and the reaction was stirred 10 min at this temperature. K2CO3 sat sol (100 ml) was added and the mixture extracted with DCM (3×100 ml). The organic phases were collected, dried over Na2SO4 and evaporated in vacuo to afford a residue which was purified by BiotageSNAP-Si column (50 g) eluting with a mixture cHex/EtOAc 95/5. Collected fractions after solvent evaporation afforded the title compound (D31) (2.1 g).

Workup

  1. additionwas added dropwise
  2. extractionwater (50 ml) and the reaction extracted with Et2O (3×100 ml)
  3. dry with materialdried over Na2SO4
  4. customevaporated in vacuo
  5. customto afford a residue which
  6. additionwas added
  7. extractionthe mixture extracted with DCM (3×100 ml)
  8. customThe organic phases were collected
  9. dry with materialdried over Na2SO4
  10. customevaporated in vacuo
  11. customto afford a residue which
  12. customwas purified by BiotageSNAP-Si column (50 g)
  13. washeluting with a mixture cHex/EtOAc 95/5
  14. customCollected fractions after solvent evaporation

Sources & evidence

ORD record
ord-5e78a34bc9cf4d00bc7e8f50e0928246
Source dataset
uspto-grants-2015_11
Patent number
US09181279B2

Reaction notes

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