Water → HCID 68533922, compound

HRID 489913Notes

Reaction equation

HRID 489913 reaction equation
O=[C:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.[NH:15]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1.C([BH3-])#N.[Na+].O>C(O)C.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[C:11]([O:10][C:8]([N:5]1[CH2:6][CH2:7][CH:2]([N:15]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)[CH2:3][CH2:4]1)=[O:9])([CH3:14])([CH3:13])[CH3:12]

Participants

7

Reactant 4

HCID 962WaterHCID 8119AzepaneHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 5003444Sodium cyanoborohydride

Product 1

HCID 68533922HCID 68533922, compoundYield 26%

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 702EthanolSolvent

Procedure

A mixture of tert-butyl 4-oxo-1-piperidinecarboxylate (10 mmol, 1.99 mmol), azepane (10 mmol, 990 mg) and titanium isopropoxide (12.5 mmol, 3.7 mL) was stirred at room temperature for 50 mins. A solution of sodium cyanoborohydride (7 mmol, 440 mg) in anhydrous ethanol (10 mL) was added and the solution was stirred under nitrogen at ambient temperature for 24 hr. Water (2 mL) was added and the precipitate was removed by filtration through Celite®, rinsing through with ethanol. The solvent was removed under vacuum and the residue purified by chromatography on silica gel eluting with a 5%-10% methanol-dichloromethane gradient to give 4-azepan-1-yl-piperidine-1-carboxylic acid tert-butyl ester (726 mg, 26%).

Workup

  1. stirringthe solution was stirred under nitrogen at ambient temperature for 24 hr
  2. customthe precipitate was removed by filtration through Celite®
  3. washrinsing through with ethanol
  4. customThe solvent was removed under vacuum
  5. customthe residue purified by chromatography on silica gel eluting with a 5%-10% methanol-dichloromethane gradient

Sources & evidence

ORD record
ord-fd1a28b354464d2db0916ce1cd9d42ec
Source dataset
uspto-grants-2005_12
Patent number
US06979741B2

Reaction notes

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