Dichloromethane → 2,7-Diazaspiro[4.5]decan-1-one
Reaction equation
FC(F)(F)C(O)=O.C([NH:27][CH2:28][CH2:29][C:30]1([C:43]([O:45]CC)=O)[CH2:35][CH2:34][CH2:33][N:32](C(OC(C)(C)C)=O)[CH2:31]1)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(Cl)Cl.O1CCOCC1.C(N(CC)C(C)C)(C)C>>[C:43]1(=[O:45])[C:30]2([CH2:35][CH2:34][CH2:33][NH:32][CH2:31]2)[CH2:29][CH2:28][NH:27]1Participants
6
Procedure
Trifluoroacetic acid (1.0 mL, 0.013 mol) was added to a solution of 1-tert-butyl 3-ethyl 3-[2-(tritylamino)ethyl]piperidine-1,3-dicarboxylate (0.10 g, 0.00018 mol) in methylene chloride (1.0 mL, 0.016 mol) and the mixture was stirred for 1 h at rt to remove the Boc and trityl groups. Then the solvent was removed under vacuum and to the resultant residue was added 1,4-dioxane (3.0 mL, 0.038 mol) followed by N,N-diisopropylethylamine (0.13 mL, 0.00074 mol) and the resultant mixture was stirred at 150° C. (microwave) for 1 h. The solvent from the mixture was removed under vacuum and the crude product was used in the next step without further purification. LC-MS: 155.2 (M+H)+.
Workup
- customto remove the Boc and trityl groups
- customThen the solvent was removed under vacuum and to the resultant residue
- customThe solvent from the mixture was removed under vacuum
- customthe crude product was used in the next step without further purification
Sources & evidence
- ORD record
- ord-9456344c1ac24d67bb2ab54c5f6c8342
- Source dataset
- uspto-grants-2012_02
- Patent number
- US08110581B2
Reaction notes
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