Allyl bromide → tert-Butyl 9-(allyloxy)-3-azaspiro[5.5]undecane-3-carboxylate
Reaction equation
[OH-].[K+].[CH2:3](Br)[CH:4]=[CH2:5].C1OCCOCCOCCOCCOCCOC1.[OH:25][CH:26]1[CH2:43][CH2:42][C:29]2([CH2:34][CH2:33][N:32]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:31][CH2:30]2)[CH2:28][CH2:27]1>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH2:3]([O:25][CH:26]1[CH2:27][CH2:28][C:29]2([CH2:34][CH2:33][N:32]([C:35]([O:37][C:38]([CH3:39])([CH3:40])[CH3:41])=[O:36])[CH2:31][CH2:30]2)[CH2:42][CH2:43]1)[CH:4]=[CH2:5]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
KOH (257.46 mmol, 21.0 eq.), allyl bromide (36.8 mmol, 3.0 eq.) and 18-crown-6 (4.9 mmol, 0.4 eq.) were added to a solution of tert-butyl 9-hydroxy-3-azaspiro[5.5]undecane-3-carboxylate (12.26 mmol, 1.0 eq.) in toluene (65 ml) at 0° C. and then reaction mixture was heated at reflux for 1 h. Then the reaction mixture was diluted with ethyl acetate (150 ml) and washed with water (150 ml) and brine (150 ml). The organic layer was dried over sodium sulfate and concentrated under reduced pressure to yield the crude product which was purified by silica gel column chromatography eluting with 10% ethyl acetate in hexanes to afford the desired product as a yellow oil. Yield: 92%
Workup
- customreaction mixture
- temperaturewas heated
- temperatureat reflux for 1 h
- washwashed with water (150 ml) and brine (150 ml)
- dry with materialThe organic layer was dried over sodium sulfate
- concentrationconcentrated under reduced pressure
- customto yield the crude product which
- customwas purified by silica gel column chromatography
- washeluting with 10% ethyl acetate in hexanes
Sources & evidence
- ORD record
- ord-d9acd396457d4d4797203064438c402c
- Source dataset
- uspto-grants-2013_06
- Patent number
- US08455475B2
Reaction notes
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