Hydrochloric Acid → 8-Tert-butyl-10-ethyl-11-oxa-3,8-diazaspiro[5.5]undecane

HRID 72913Notes

Reaction equation

HRID 72913 reaction equation
[C:1]([N:5]1[CH2:22][CH:21]([CH2:23][CH3:24])[O:20][C:7]2([CH2:12][CH2:11][N:10](C(OC(C)(C)C)=O)[CH2:9][CH2:8]2)[CH2:6]1)([CH3:4])([CH3:3])[CH3:2].Cl.O1CCOCC1>ClCCl>[C:1]([N:5]1[CH2:22][CH:21]([CH2:23][CH3:24])[O:20][C:7]2([CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH2:6]1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 70872875HCID 70872875, compound

Product 1

HCID 682920458-Tert-butyl-10-ethyl-11-oxa-3,8-diazaspiro[5.5]undecaneYield 104%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Tert-butyl 8-tert-butyl-10-ethyl-11-oxa-3,8-diazaspiro[5.5]undecane-3-carboxylate (530 mg, 1.56 mmol) was dissolved in dichloromethane and treated with a solution of HCl in dioxane (8.0 mL of 4 M, 33 mmol) and stirred for 15 min. The reaction mixture was diluted with dichloromethane and washed with 1:1 saturated NaHCO3/1 M NaOH. The organic layer was dried over Na2SO4, filtered and concentrated to provide 8-tert-butyl-10-ethyl-11-oxa-3,8-diazaspiro[5.5]undecane (390 mg, 99%) as an oily solid. ESI-MS m/z calc. 240.2. Found 241.3 (M+1)+; Retention time: 0.21 minutes (3 min run).

Workup

  1. washwashed with 1:1 saturated NaHCO3/1 M NaOH
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-ae7e456c2bfa471c80e0c16ce35eef41
Source dataset
uspto-grants-2014_09
Patent number
US08828996B2

Reaction notes

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