Water → tert-Butyl 8-oxo-5-azaspiro(2.5)octane-5-carboxylate

HRID 1867398Notes

Reaction equation

HRID 1867398 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](=[O:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:15](O[K])(C)(C)[CH3:16].[I-].ClCC[S+](C)C.O>CC(O)(C)C.C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][C:11](=[O:14])[C:12]2([CH2:16][CH2:15]2)[CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 962WaterHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 10912030(2-Chloroethyl)diMethylsulfoniuM iodideHCID 178418922HCID 178418922, compound

Product 1

HCID 57889898tert-Butyl 8-oxo-5-azaspiro(2.5)octane-5-carboxylateYield 19%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6386tert-ButanolSolvent

Procedure

4-Oxo-piperidine-1-carboxylic acid tert-butyl ester (1.0 g, 5 mmol) was dissolved in tBuOH (10 ml) with tBuOK (1.1 g, 10 mmol) and stirred for 15 minutes before portionwise addition of (2-chloro-ethyl)-dimethyl-sulfonium iodide (Tet. Lett. 1984, 25, 5501) (1.1 g, 5 mmol) over 1 h. The reaction was stirred for 16 h after which time it was partioned between water and CH2Cl2, the organic collected, dried (Na2SO4) and concentrated. Flash column chromatography (EtOAc:n-heptane 1:9-3:7) afforded the titled product (0.2 g, 19%) as a colourless oil. MS: 130.1 (MH+).

Workup

  1. dry with materialthe organic collected, dried (Na2SO4)
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-6da87897b5444ffeb422b22beb144bc1
Source dataset
uspto-grants-2009_12
Patent number
US07632829B2

Reaction notes

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