Potassium Carbonate → Tert-butyl 2-(methoxymethyl)-4-(2-oxopropyl)-1-oxa-4,9-diazaspiro[5.5]undecane-9-carboxylate

HRID 713003Notes

Reaction equation

HRID 713003 reaction equation
[CH3:1][O:2][CH2:3][CH:4]1[O:21][C:8]2([CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)[CH2:7][NH:6][CH2:5]1.C([O-])([O-])=O.[K+].[K+].Br[CH2:29][C:30](=[O:32])[CH3:31]>C(#N)C.ClCCl>[CH3:1][O:2][CH2:3][CH:4]1[CH2:5][N:6]([CH2:29][C:30](=[O:32])[CH3:31])[CH2:7][C:8]2([CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:18])([CH3:20])[CH3:19])=[O:15])[CH2:10][CH2:9]2)[O:21]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 11715BromoacetoneHCID 70872666Tert-butyl 10-(methoxymethyl)-11-oxa-3,8-diazaspiro[5.5]undecane-3-carboxylate

Product 1

HCID 68291584Tert-butyl 2-(methoxymethyl)-4-(2-oxopropyl)-1-oxa-4,9-diazaspiro[5.5]undecane-9-carboxylate

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

To a mixture of tert-butyl 10-(methoxymethyl)-11-oxa-3,8-diazaspiro[5.5]undecane-3-carboxylate and K2CO3 (115 mg, 0.832 mmol) in acetonitrile (1.4 mL) was added 1-bromopropan-2-one (304 mg, 2.00 mmol). The reaction mixture was heated under argon in a sealed tube for 16 h. The mixture was cooled, diluted with dichloromethane and washed with water. The organic layer was dried over Na2SO4, filtered and concentrated in vacuo to provide tert-butyl 2-(methoxymethyl)-4-(2-oxopropyl)-1-oxa-4,9-diazaspiro[5.5]undecane-9-carboxylate. ESI-MS m/z calc. 356.2. found 357.3 (M+1)+; Retention time: 0.98 minutes (3 min run).

Workup

  1. temperatureThe reaction mixture was heated under argon in a sealed tube for 16 h
  2. temperatureThe mixture was cooled
  3. washwashed with water
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-79f1c836e22846ecbe1d511ecd5b7b31
Source dataset
uspto-grants-2015_11
Patent number
US09181273B2

Reaction notes

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