Sulfoxonium, trimethyl-, iodide (1:1) → tert-Butyl 1-oxa-6-azaspiro(2.5)octane-6-carboxylate

HRID 2202337Notes

Reaction equation

HRID 2202337 reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.[CH3:15]C(C)([O-])C.[K+].[I-].C[S+](C)(C)=O>C(O)CCC>[O:1]1[C:2]2([CH2:3][CH2:4][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:6][CH2:7]2)[CH2:15]1

Participants

5

Reactant 3

HCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 23665647Potassium tert-butoxide

Product 1

HCID 22135564tert-Butyl 1-oxa-6-azaspiro(2.5)octane-6-carboxylate

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of tert-butyl 4-oxopiperidine-1-carboxylate (5 g, 25 mmol) in BuOH (20 mL) was added potassium tert-butoxide (4.125 g, 18.75 mmol). The mixture was stirred at 50° C. for 1 h. Then trimethyl sulfoxonium iodide (11 g, 50 mmol) was added to the mixture, and the resulting reaction mixture was stirred at 50° C. overnight. When TLC showed that s.m. was consumed, the mixture was cooled and filtered. The filtrate was concentrated to give the crude product which was used in the next step without further purification.

Workup

  1. customthe resulting reaction mixture
  2. stirringwas stirred at 50° C. overnight
  3. customwas consumed
  4. temperaturethe mixture was cooled
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-0668f51550ce47ac9b220140fde34b7a
Source dataset
uspto-grants-2016_06
Patent number
US09365545B2

Reaction notes

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