Potassium tert-butoxide → HCID 89814013, compound

HRID 525336Notes

Reaction equation

HRID 525336 reaction equation
CC(C)([O-])C.[K+].OC(C)(C)[CH:9]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])C)[C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1>C1COCC1.C(Cl)Cl>[CH3:22][C:19]1([CH3:21])[O:18][C:17](=[O:23])[NH:16][CH:9]1[C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 131735587HCID 131735587, compound

Product 1

HCID 89814013HCID 89814013, compoundYield 103.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Potassium tert-butoxide (0.093 g, 0.826 mmol) was added to a 0° C. solution of tert-butyl (2-hydroxy-2-methyl-1-(pyridin-3-yl)propyl)carbamate (0.200 g, 0.751 mmol) in THF (5.0 mL). The ice bath was removed and the reaction mixture was stirred at room temperature for 16 hours. The reaction mixture was concentrated to afford a yellow oil. The residual yellow oil was dissolved in DCM and passed through a Silycycle SCX column washing with MeOH and then with 7 N ammonia in MeOH. The ammonia solution was concentrated to afford 5,5-dimethyl-4-(pyridin-3-yl)oxazolidin-2-one (0.150 g, 0.780 mmol, 100% yield) as a pale yellow oil. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.82 (s, 3H), 1.53 (s, 3H), 4.74 (s, 1H), 7.44 (ddd, J=7.90, 4.77, 0.64 Hz, 1H), 7.64-7.78 (m, 1H), 8.08 (s, 1H), 8.51 (d, J=2.35 Hz, 1H), 8.55 (dd, J=4.79, 1.66 Hz, 1H). m/z (ESI) 193 (M+H)+.

Workup

  1. customThe ice bath was removed
  2. concentrationThe reaction mixture was concentrated
  3. customto afford a yellow oil
  4. washwashing with MeOH
  5. concentrationThe ammonia solution was concentrated

Sources & evidence

ORD record
ord-3a4cff0474a84435a7be1046b41e4e06
Source dataset
uspto-grants-2016_05
Patent number
US09340549B2

Reaction notes

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