Trifluoroacetic acid → Benzyl morpholine-2-carboxylate
Reaction equation
[N:1]1(C(OC(C)(C)C)=O)[CH2:6][CH2:5][O:4][CH:3]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[CH2:2]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH:1]1[CH2:6][CH2:5][O:4][CH:3]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[CH2:2]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
In a 500-mL round-bottom flask, 2-benzyl 4-tert-butyl morpholine-2,4-dicarboxylate (7.94 g, 25 mmol) was dissolved in DCM (200 mL). It was then cooled to 0° C. TFA (15 ml, 198 mmol) was added via pipet, and the solution was allowed to warm naturally to ambient temperature in the ice bath, whereupon it was stirred for 14 h. The mixture was concentrated to afford the title compound (50% by weight with the remainder assumed to be TFA, 10.86 g, 24 mmol). MS m/z 222 (M+1).
Workup
- concentrationThe mixture was concentrated
Sources & evidence
- ORD record
- ord-8fc0ce8f281143528c92f275bfadad2f
- Source dataset
- uspto-grants-2011_01
- Patent number
- US07872009B2
Reaction notes
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