Water → benzyl(R)-3-[(R)-1-(naphthalen-1-yl)ethylamino]piperidine-1-carboxylate

HRID 1811653Notes

Reaction equation

HRID 1811653 reaction equation
ClC([N:4]([C@@H:21]([C:23]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=[CH:25][CH:24]=1)[CH3:22])[C@@H:5]1[CH2:10][CH2:9][CH2:8][N:7]([C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:12])[CH2:6]1)=O.O>O1CCCC1>[C:23]1([C@H:21]([NH:4][C@@H:5]2[CH2:10][CH2:9][CH2:8][N:7]([C:11]([O:13][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[O:12])[CH2:6]2)[CH3:22])[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 962WaterHCID 58973551benzyl(R)-3-[chlorocarbonyl-(R)-1-(naphthalen-1-yl)ethylamino]piperidine-1-carboxylate

Product 1

HCID 58973486benzyl(R)-3-[(R)-1-(naphthalen-1-yl)ethylamino]piperidine-1-carboxylateYield 51.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution containing 54.6 g of benzyl(R)-3-[chlorocarbonyl-(R)-1-(naphthalen-1-yl)ethylamino]piperidine-1-carboxylate dissolved in 700 ml of tetrahydrofuran was added 350 ml of water, and the mixture was stirred under reflux for 15 hours. After tetrahydrofuran was evaporated, a saturated aqueous sodium bicarbonate solution and chloroform were added thereto, the mixture was stirred and the liquids were separated. The organic layer was dried and concentrated, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1→0:1) to obtain 24.3 g of benzyl(R)-3-[(R)-1-(naphthalen-1-yl)ethylamino]piperidine-1-carboxylate.

Workup

  1. temperatureunder reflux for 15 hours
  2. customAfter tetrahydrofuran was evaporated
  3. additiona saturated aqueous sodium bicarbonate solution and chloroform were added
  4. stirringthe mixture was stirred
  5. customthe liquids were separated
  6. customThe organic layer was dried
  7. concentrationconcentrated
  8. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1→0:1)

Sources & evidence

ORD record
ord-0b5dc2227fa649b4907f32531be23ea6
Source dataset
uspto-grants-2013_01
Patent number
US08362274B2

Reaction notes

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