HCID 68291610, compound → 4-Benzyl-2-phenyl-1-oxa-4,9-diazaspiro[5.5]undecane

HRID 72863Notes

Reaction equation

HRID 72863 reaction equation
[CH2:1]([N:8]([CH2:18][C:19]1(O)[CH2:24][CH2:23][N:22](C(OC(C)(C)C)=O)[CH2:21][CH2:20]1)[CH2:9][CH:10]([OH:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>Br>[CH2:1]([N:8]1[CH2:18][C:19]2([CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)[O:17][CH:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 68291610HCID 68291610, compound

Product 1

HCID 682909524-Benzyl-2-phenyl-1-oxa-4,9-diazaspiro[5.5]undecaneYield 97%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Conditions

Temperature
55 °C

Procedure

To tert-butyl 4-[[benzyl-(2-hydroxy-2-phenyl-ethyl)amino]methyl]-4-hydroxy-piperidine-1-carboxylate (6.2 g, 14.07 mmol) was added HBr (60 mL of 48% w/w,) and the reaction mixture was stirred at 55° C. for 10 hours. The reaction mixture was evaporated in vacuo, basified the aqueous with 50% aq. NaOH to pH13, then extracted with DCM (3×75 mL). The combined organics were dried over MgSO4, filtered and concentrated in vacuo to give 4-benzyl-2-phenyl-1-oxa-4,9-diazaspiro[5.5]undecane (4.4 g, 97%) as a yellow oil, which was used directly without further purification. ESI-MS m/z calc. 322.2. Found 323.7 (M+1)+; Retention time: 1.72 minutes (3 min run).

Workup

  1. customThe reaction mixture was evaporated in vacuo
  2. extractionextracted with DCM (3×75 mL)
  3. dry with materialThe combined organics were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f3c941328d4b4c9a8a9bf7894a9fc7cf
Source dataset
uspto-grants-2014_09
Patent number
US08828996B2

Reaction notes

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