Triethylamine → Ethyl 2-methyl-2-(1-oxo-2,8-diazaspiro[4.5]decan-8-yl)propanoate
Reaction equation
[C:1]1(=[O:11])[C:5]2([CH2:10][CH2:9][NH:8][CH2:7][CH2:6]2)[CH2:4][CH2:3][NH:2]1.C(N(CC)CC)C.Br[C:20]([CH3:27])([CH3:26])[C:21]([O:23][CH2:24][CH3:25])=[O:22]>>[CH3:26][C:20]([N:8]1[CH2:9][CH2:10][C:5]2([C:1](=[O:11])[NH:2][CH2:3][CH2:4]2)[CH2:6][CH2:7]1)([CH3:27])[C:21]([O:23][CH2:24][CH3:25])=[O:22]Participants
4
Conditions
- Temperature
- 80 °C
Procedure
A mixture of 2,8-diazaspiro[4.5]decan-1-one (3.03 g, 19.65 mmol), triethylamine (5.48 ml, 39.3 mmol) and ethyl 2-bromo-2-methylpropanoate (5.77 ml, 39.3 mmol) was heated at 80° C. overnight. The reaction mixture was partitioned between methylene chloride (200 mL) and saturated sodium bicarbonate, the alkaline phase was extracted with methylene chloride (3×100 mL). The combined organic phase was dried over magnesium sulfate, concentrated and the residue was purified on silica gel using methanol/methylene chloride to give the title compound. LC/MS (M+1)+: 269.4
Workup
- customThe reaction mixture was partitioned between methylene chloride (200 mL) and saturated sodium bicarbonate
- extractionthe alkaline phase was extracted with methylene chloride (3×100 mL)
- dry with materialThe combined organic phase was dried over magnesium sulfate
- concentrationconcentrated
- customthe residue was purified on silica gel
Sources & evidence
- ORD record
- ord-11a1671d624d468c82dec85c1c40fb58
- Source dataset
- uspto-grants-2015_12
- Patent number
- US09206198B2
Reaction notes
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