Sodium Hydroxide → Ethyl([1,4']bipiperidinyl-4-yloxy)-acetate

HRID 730641Notes

Reaction equation

HRID 730641 reaction equation
[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].O=[C:16]1[CH2:21][CH2:20][N:19](C(OC(C)(C)C)=O)[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])(C)C)=[O:38])[CH2:31][CH2:30]1.[OH-].[Na+]>C1COCC1>[N:29]1([CH:16]2[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)[CH2:30][CH2:31][CH:32]([O:35][CH2:36][C:37]([O:39][CH2:40][CH3:43])=[O:38])[CH2:33][CH2:34]1

Participants

6

Reactant 4

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

Product 1

HCID 57807779Ethyl([1,4']bipiperidinyl-4-yloxy)-acetate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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

  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)

Sources & evidence

ORD record
ord-196fc458c08140fa9742debef6d445a4
Source dataset
uspto-grants-2009_09
Patent number
US07582625B2

Reaction notes

Loading…