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

HRID 72917Notes

Reaction equation

HRID 72917 reaction equation
[C:1]([N:5]1[CH2:22][CH:21]([CH2:23][O:24][CH3:25])[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][O:24][CH3:25])[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 70872449Tert-butyl 8-tert-butyl-10-(methoxymethyl)-11-oxa-3,8-diazaspiro[5.5]undecane-3-carboxylate

Product 1

HCID 682918248-Tert-butyl-10-(methoxymethyl)-11-oxa-3,8-diazaspiro[5.5]undecaneYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Tert-butyl 8-tert-butyl-10-(methoxymethyl)-11-oxa-3,8-diazaspiro[5.5]undecane-3-carboxylate (732 mg, 2.05 mmol) was dissolved in dichloromethane (10 mL) and treated dropwise with a solution of HCl in dioxane (12.8 mL of 4 M, 51.3 mmol). The reaction was stirred for 1.5 h and then diluted with dichloromethane. The organic phase was washed with 1:1 saturated NaHCO3/1 M NaOH, dried over Na2SO4 and concentrated to provide 8-tert-butyl-10-(methoxymethyl)-11-oxa-3,8-diazaspiro[5.5]undecane (526 mg, 2.05 mmol, 99%) as a viscous amber colored oil. ESI-MS m/z calc. 256.2. Found 257.3 (M+1)+; Retention time: 0.2 minutes (3 min run). 1H NMR (400 MHz, CDCl3) δ 3.88-3.71 (m, 1H), 3.43-3.38 (m, 1H), 3.37 (d, J=2.5 Hz, 3H), 3.35-3.30 (m, 1H), 3.24 (td, J=12.2, 3.4 Hz, 1H), 3.15-3.07 (m, 1H), 3.02 (td, J=12.2, 3.0 Hz, 1H), 2.93-2.84 (m, 1H), 2.78-2.68 (m, 1H), 2.58 (d, J=8.9 Hz, 2H), 2.48-2.19 (m, 1H), 1.97 (d, J=11.4 Hz, 1H), 1.92 (ddd, J=16.6, 12.2, 9.6 Hz, 2H), 1.84-1.74 (m, 1H), 1.70-1.55 (m, 2H), 1.00 (s, 9H).

Workup

  1. washThe organic phase was washed with 1:1 saturated NaHCO3/1 M NaOH
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-fe6d35235f8c46fead39a355eef4062f
Source dataset
uspto-grants-2014_09
Patent number
US08828996B2

Reaction notes

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