Potassium Carbonate → (R)-tert-butyl 3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)pyrrolidine-1-carboxylate

HRID 873336Notes

Reaction equation

HRID 873336 reaction equation
CS([O:5][C@H:6]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7]1)(=O)=O.[CH3:18][C:19]1([CH3:33])[C:23]([CH3:25])([CH3:24])[O:22][B:21]([C:26]2[CH:31]=[CH:30][C:29](O)=[CH:28][CH:27]=2)[O:20]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:24][C:23]1([CH3:25])[C:19]([CH3:18])([CH3:33])[O:20][B:21]([C:26]2[CH:31]=[CH:30][C:29]([O:5][C@@H:6]3[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7]3)=[CH:28][CH:27]=2)[O:22]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27346244-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenolHCID 11032777(S)-1-Boc-3-methanesulfonyloxy-pyrrolidine

Product 1

HCID 86710535(R)-tert-butyl 3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)pyrrolidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(S)-tert-Butyl 3-((methylsulfonyl)oxy)pyrrolidine-1-carboxylate (0.53 g, 2.0 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (0.48 g, 2.2 mmol) and K2CO3 (0.33 g, 2.4 mmol) in DMF (5 mL) were heated at 85° C. for 1 d. The reaction mixture was concentrated in vacuo and Et2O and water were added. The aqueous phase was extracted with Et2O and the combined organics were washed with 1 M NaOH solution (aq), dried (MgSO4), filtered and concentrated in vacuo to give (R)-tert-butyl 3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)pyrrolidine-1-carboxylate which was used in the next step without further purification.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo and Et2O and water
  2. additionwere added
  3. extractionThe aqueous phase was extracted with Et2O
  4. washthe combined organics were washed with 1 M NaOH solution (aq)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d6bd65d01e0a4ea3ac7958b5a2f00cf3
Source dataset
uspto-grants-2015_03
Patent number
US08975406B2

Reaction notes

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