Hydrochloric Acid → HCID 68291624, compound

HRID 712950Notes

Reaction equation

HRID 712950 reaction equation
[CH2:1]([N:8]1[CH2:13][C:12]([CH3:15])([CH3:14])[O:11][C:10]2([CH2:20][CH2:19][N:18](C(OC(C)(C)C)=O)[CH2:17][CH2:16]2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>C(O)C>[CH2:1]([N:8]1[CH2:13][C:12]([CH3:15])([CH3:14])[O:11][C:10]2([CH2:20][CH2:19][NH:18][CH2:17][CH2:16]2)[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68291365HCID 68291365, compound

Product 1

HCID 68291624HCID 68291624, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To tert-butyl 2-benzyl-4,4-dimethyl-5-oxa-2,9-diazaspiro[5.5]undecane-9-carboxylate (560 mg, 1.50 mmol) was added hydrogen chloride (7.5 mL of 4 M in dioxane, 29.90 mmol), followed by ethanol (2 mL) and the reaction mixture was stirred for 30 minutes. The reaction mixture was concentrated in vacuo, dissolved in water (5 mL), washed with methyl tert-butyl ether (5 mL), basified with solid NaHCO3 then adjusted to pH 13-14 with 50% aq. NaOH. The aqueous layer was extracted with ethyl acetate (3×25 mL), dried over MgSO4 and concentrated to give 2-benzyl-4,4-dimethyl-5-oxa-2,9-diazaspiro[5.5]undecane (400 mg, 98%) as a yellow oil, which was used directly without further purification. ESI-MS m/z calc. 274.4. found 275.5 (M+1)+; Retention time: 0.75 minutes (3 min run).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutiondissolved in water (5 mL)
  3. washwashed with methyl tert-butyl ether (5 mL)
  4. extractionThe aqueous layer was extracted with ethyl acetate (3×25 mL)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-38fb942f6cfd4798be46b1f6ddf4f9e5
Source dataset
uspto-grants-2015_11
Patent number
US09181273B2

Reaction notes

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