Tetrahydrofuran → tert-Butyl cis(+/-)-4-{benzyl[(benzyloxy)carbonyl]amino}-3-methoxypiperidine-1-carboxylate

HRID 1425438Notes

Reaction equation

HRID 1425438 reaction equation
C1COCC1.[CH2:6]([NH:13][C@H:14]1[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][C@H:15]1[O:27][CH3:28])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(=O)(O)[O-].[Na+].Cl[C:35]([O:37][CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)=[O:36]>O>[CH2:6]([N:13]([C:35]([O:37][CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)=[O:36])[C@H:14]1[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:24])([CH3:25])[CH3:26])=[O:21])[CH2:16][C@H:15]1[O:27][CH3:28])[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 10387Benzyl chloroformateHCID 516892Sodium BicarbonateHCID 86648851Tert-butyl cis(+/-)-4-benzylamino-3-methoxypiperidine-1-carboxylate

Product 1

HCID 86648850tert-Butyl cis(+/-)-4-{benzyl[(benzyloxy)carbonyl]amino}-3-methoxypiperidine-1-carboxylateYield 46.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

THF (16 mL) and water (4 mL) were added to tert-butyl cis(±)-4-benzylamino-3-methoxypiperidine-1-carboxylate obtained in Example (259a) (1.00 g, 3.1 mmol). While the mixture was stirred, saturated aqueous sodium bicarbonate solution (4 mL) and benzyl chloroformate (0.96 g, 5.6 mmol) were added at room temperature, followed by stirring overnight. The reaction solution was diluted with water, followed by extraction with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: ethyl acetate/hexane=1/9, 1/1) to obtain 0.66 g of the title compound as a colorless oily substance (58%).

Workup

  1. stirringby stirring overnight
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (elution solvent: ethyl acetate/hexane=1/9, 1/1)

Sources & evidence

ORD record
ord-30e7fc152c8241c8ac6f93333983c5c5
Source dataset
uspto-grants-2015_01
Patent number
US08927588B2

Reaction notes

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