Tetrahydrofuran → Benzyl 4-tert-butoxycarbonylmethoxy-[1,4']bipiperidinyl-1'-carboxylate
Reaction equation
[BH-](O[C:11]([CH3:13])=O)(OC(C)=O)OC(C)=O.[Na+].O=[C:16]1[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])(C)C)=[O:23])[CH2:18][CH2:17]1.[NH:29]1[CH2:34][CH2:33][CH:32]([O:35][CH2:36][C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH2:31][CH2:30]1.[OH-].[Na+].[CH2:46]1[CH2:50]OC[CH2:47]1>>[C:40]([O:39][C:37]([CH2:36][O:35][CH:32]1[CH2:31][CH2:30][N:29]([CH:16]2[CH2:17][CH2:18][N:19]([C:22]([O:24][CH2:25][C:28]3[CH:13]=[CH:11][CH:50]=[CH:46][CH:47]=3)=[O:23])[CH2:20][CH2:21]2)[CH2:34][CH2:33]1)=[O:38])([CH3:43])([CH3:42])[CH3:41]Participants
6
Procedure
2.90 g (13.3 mmol) NaBH(OAc)3 were added batchwise to a solution of 2.58 g (11.1 mmol)) tert.butyl 4-oxo-piperidine-1-carboxylate and 2.80 g (12.4 mmol) tert.butyl (piperidin-4-yloxy)-acetate in 30 mL THF and the reaction mixture was stirred overnight at RT. 50 mL of 1 M NaOH was added, the mixture was stirred for 1 h at RT, extracted exhaustively with EtOAc and the combined organic phases were dried on Na2SO4. After the elimination of the desiccant and solvent the residue was purified by chromatography (Alox, activity stage II-III, DCM/MeOH 100:1).
Workup
- stirringthe mixture was stirred for 1 h at RT
- extractionextracted exhaustively with EtOAc
- customthe combined organic phases were dried on Na2SO4
- customAfter the elimination of the desiccant and solvent the residue was purified by chromatography (Alox, activity stage II-III, DCM/MeOH 100:1)
Sources & evidence
- ORD record
- ord-7859b5c8cf4d4bbf9d79796c1d0ed312
- Source dataset
- uspto-grants-2011_03
- Patent number
- US07897603B2
Reaction notes
Loading…