Chloroiodomethane → Tert-butyl 6-azaspiro[2.5]octane-6-carboxylate

HRID 1867394Notes

Reaction equation

HRID 1867394 reaction equation
[Zn]([CH2:4][CH3:5])CC.ClCI.[C:9]([O:13][C:14]([N:16]1[CH2:21][CH2:20][C:19](=[CH2:22])[CH:18](O)C1)=[O:15])([CH3:12])([CH3:11])[CH3:10]>ClCCCl>[C:9]([O:13][C:14]([N:16]1[CH2:5][CH2:4][C:19]2([CH2:18][CH2:22]2)[CH2:20][CH2:21]1)=[O:15])([CH3:10])([CH3:11])[CH3:12]

Participants

5

Reactant 3

HCID 11644ChloroiodomethaneHCID 10584700tert-Butyl 3-hydroxy-4-methylidenepiperidine-1-carboxylateHCID 178418750HCID 178418750, compound

Product 1

HCID 51358341Tert-butyl 6-azaspiro[2.5]octane-6-carboxylateYield 56,791.102%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of Et2Zn (37.5 ml, 1.1M solution in toluene, 0.04 mmol) in DCE (80 ml) at 0° C. was added chloroiodomethane (5.99 ml, 0.08 mmol) under Ar. This mixture was stirred for 15 minutes before a solution of 3-hydroxy-4-methylene-piperidine-1-carboxylic acid tert-butyl ester (J. Org. Chem. 2001, 66, 2487) (4.19 g, 0.02 mmol) in DCE (10 ml) was added, after which time the reaction was stirred for 0.5 h at 0° C. and then allowed to reach room temperature, stirring for a further 1 h. The reaction was then quenched by addition of saturated NH4Cl, separated, and the organic dried (Na2SO4) and concentrated. Purfication by flash column chromatography (EtOAc:n-heptane 2:8-1:1) afforded the title product (2.4 g, 54%) as a crystalline solid. MS: 228.2 (MH+).

Workup

  1. additionwas added
  2. customto reach room temperature
  3. stirringstirring for a further 1 h
  4. customThe reaction was then quenched by addition of saturated NH4Cl
  5. customseparated
  6. dry with materialthe organic dried (Na2SO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-bb46dd21d08e46fbbcbebeded30e82c4
Source dataset
uspto-grants-2009_12
Patent number
US07632829B2

Reaction notes

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