benzyl(R)-3-[(R)-1-(naphthalen-1-yl)ethylamino]piperidine-1-carboxylate → (R)-3-[(R)-1-(naphthalen-1-yl)ethylamino]piperidine
Reaction equation
[C:1]1([C@H:11]([NH:13][C@@H:14]2[CH2:19][CH2:18][CH2:17][N:16](C(OCC3C=CC=CC=3)=O)[CH2:15]2)[CH3:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1>CO.[C].[Pd]>[C:1]1([C@H:11]([NH:13][C@@H:14]2[CH2:19][CH2:18][CH2:17][NH:16][CH2:15]2)[CH3:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1Participants
Procedure
To a solution containing 24.2 g of benzyl(R)-3-[(R)-1-(naphthalen-1-yl)ethylamino]piperidine-1-carboxylate dissolved in 250 ml of methanol was added 2.5 g of palladium carbon (10% wet), and the mixture was shaked under hydrogen atmosphere at 3 atm at room temperature for 40 hours. Palladium carbon was removed, and the solvent was evaporated, the residue washed with ethyl acetate-chloroform (10:1), and collected by filtration to obtain 15.3 g of (R)-3-[(R)-1-(naphthalen-1-yl)ethylamino]-piperidine (the following Reference example Table, Reference example 3.001(a)). MS·APCI (m/z): 255 [M+H]+ (7) By using 14.5 g of benzyl(S)-3-[chlorocarbonyl-(R)-1-(naphthalen-1-yl)ethylamino]piperidine-1-carboxylate, the same treatment was carried out as in the above-mentioned (5) to obtain 4.74 g of benzyl(S)-3-[(R)-1-(naphthalen-1-yl)ethylamino]piperidine-1-carboxylate. MS·APCI (m/z): 389 [M+H]+
Workup
- customPalladium carbon was removed
- customthe solvent was evaporated
- washthe residue washed with ethyl acetate-chloroform (10:1)
- filtrationcollected by filtration
Sources & evidence
- ORD record
- ord-84b7e4c3a95f42adbe101517c890f510
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08362274B2
Reaction notes
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