Potassium Carbonate → tert-butyl-4-(3-(4-(5-methyl-1H-tetrazol-1-yl)phenoxy)-2-oxopyrrolidin-1-yl)piperidine-1-carboxylate

HRID 407950Notes

Reaction equation

HRID 407950 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[CH2:18][CH2:17][C@@H:16]([O:19]S(C)(=O)=O)[C:15]2=[O:24])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:25][C:26]1[N:30]([C:31]2[CH:36]=[CH:35][C:34](O)=[CH:33][CH:32]=2)[N:29]=[N:28][N:27]=1.C([O-])([O-])=O.[K+].[K+]>CS(C)=O.O.CCOC(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[CH2:18][CH2:17][CH:16]([O:19][C:34]3[CH:35]=[CH:36][C:31]([N:30]4[C:26]([CH3:25])=[N:27][N:28]=[N:29]4)=[CH:32][CH:33]=3)[C:15]2=[O:24])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 167651684-(5-methyl-1H-tetrazol-1-yl)phenolHCID 86688072(R)-tert-butyl 4-(3-(methylsulfonyloxy)-2-oxopyrrolidin-1-yl)piperidine-1-carboxylate

Product 1

HCID 86688101tert-butyl-4-(3-(4-(5-methyl-1H-tetrazol-1-yl)phenoxy)-2-oxopyrrolidin-1-yl)piperidine-1-carboxylateYield 52%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of (R)-tert-butyl-4-(3-(methylsulfonyloxy)-2-oxopyrrolidin-1-yl)piperidine-1-carboxylate (Preparation D; 1.03 g, 2.84 mmol) and 4-(5-methyl-1H-tetrazol-1-yl)phenol (500 mg, 2.84 mmol) in DMSO (10 mL) was added K2CO3 (1.18 g, 8.51 mmol). The reaction was heated to 70° C. for 12 hours and then diluted with water (10 mL) and EtOAc (10 mL). The organic layer was separated and the aqueous layer extracted with EtOAc (2×15 mL). The combined organic layers were dried with MgSO4 and concentrated in vacuo. The material was purified by silica gel chromatography eluting with 1:1 hexanes/EtOAc to EtOAc to yield tert-butyl-4-(3-(4-(5-methyl-1H-tetrazol-1-yl)phenoxy)-2-oxopyrrolidin-1-yl)piperidine-1-carboxylate (621 mg, 52%) as an off white solid.

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous layer extracted with EtOAc (2×15 mL)
  3. dry with materialThe combined organic layers were dried with MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe material was purified by silica gel chromatography
  6. washeluting with 1:1 hexanes/EtOAc to EtOAc

Sources & evidence

ORD record
ord-b55e07d0782240d5b55bb393792c164e
Source dataset
uspto-grants-2014_06
Patent number
US08754226B2

Reaction notes

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