Trifluoroacetic acid → 8-Ethyl-10-phenyl-11-oxa-3,8-diazaspiro[5.5]undecane

HRID 712948Notes

Reaction equation

HRID 712948 reaction equation
[CH2:1]([N:3]1[CH2:20][CH:19]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[O:18][C:5]2([CH2:10][CH2:9][N:8](C(OC(C)(C)C)=O)[CH2:7][CH2:6]2)[CH2:4]1)[CH3:2].FC(F)(F)C(O)=O>C(Cl)Cl>[CH2:1]([N:3]1[CH2:20][CH:19]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[O:18][C:5]2([CH2:10][CH2:9][NH:8][CH2:7][CH2:6]2)[CH2:4]1)[CH3:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 70872556Tert-butyl 8-ethyl-10-phenyl-11-oxa-3,8-diazaspiro[5.5]undecane-3-carboxylate

Product 1

HCID 683110928-Ethyl-10-phenyl-11-oxa-3,8-diazaspiro[5.5]undecaneYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To tert-butyl 8-ethyl-10-phenyl-11-oxa-3,8-diazaspiro[5.5]undecane-3-carboxylate (540 mg, 1.50 mmol) in DCM (1.5 mL) was added 2,2,2-trifluoroacetic acid (1 mL, 12.98 mmol) and the solution was stirred for 30 minutes. The reaction mixture was concentrated in vacuo, diluted with DCM (50 mL), washed with 1:1 sat. aq. Na2CO3/NaHCO3 (10 ml) and the aqueous was extracted further with DCM (2×25 mL). The combined organics were dried (MgSO4) and evaporated to give 8-ethyl-10-phenyl-11-oxa-3,8-diazaspiro[5.5]undecane (390 mg, 100%) as a pale yellow solid, which was used without further purification. ESI-MS m/z calc. 260.4. found 261.3 (M+1)+; Retention time: 0.3 minutes (3 min run).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additiondiluted with DCM (50 mL)
  3. washwashed with 1:1 sat. aq. Na2CO3/NaHCO3 (10 ml)
  4. extractionthe aqueous was extracted further with DCM (2×25 mL)
  5. dry with materialThe combined organics were dried (MgSO4)
  6. customevaporated

Sources & evidence

ORD record
ord-90149c3edeb64baebc28af09039e829e
Source dataset
uspto-grants-2015_11
Patent number
US09181273B2

Reaction notes

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