Tetrahydrofuran → Benzyl 4-tert-butoxycarbonylmethoxy-[1,4']bipiperidinyl-1'-carboxylate

HRID 599737Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 599737
[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]

Komponenten

6

Edukt 5

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 5049666Sodium triacetoxyborohydrideHCID 10036224Tert-butyl (piperidin-4-yloxy)-acetate

Produkt 1

HCID 66941898Benzyl 4-tert-butoxycarbonylmethoxy-[1,4']bipiperidinyl-1'-carboxylate

Versuchsvorschrift

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).

Aufarbeitung

  1. stirringthe mixture was stirred for 1 h at RT
  2. extractionextracted exhaustively with EtOAc
  3. customthe combined organic phases were dried on Na2SO4
  4. customAfter the elimination of the desiccant and solvent the residue was purified by chromatography (Alox, activity stage II-III, DCM/MeOH 100:1)

Quellen und Nachweise

ORD-Eintrag
ord-7859b5c8cf4d4bbf9d79796c1d0ed312
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07897603B2

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