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

HRID 409609ノート

反応式

HRID 409609 の反応式
[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]=1

参加物

4

反応物 1

HCID 58973486benzyl(R)-3-[(R)-1-(naphthalen-1-yl)ethylamino]piperidine-1-carboxylate

生成物 1

HCID 58973523(R)-3-[(R)-1-(naphthalen-1-yl)ethylamino]piperidine収率 96.6%

試薬・触媒・溶媒 2

HCID 178418390HCID 178418390、化合物触媒HCID 887Methanol溶媒

実験手順

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=4:140:1) to obtain 24.3 g of benzyl (R)-3-[(R)-1-(naphthalen-1-yl)ethylamino]piperidine-1-carboxylate. MS•APC I (m/z): 389 [M+H]+ (6) 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 was 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]+

後処理

  1. customPalladium carbon was removed
  2. customthe solvent was evaporated
  3. washthe residue was washed with ethyl acetate-chloroform (10:1)
  4. filtrationcollected by filtration

出典と根拠

ORDレコード
ord-2b7bdd565538420399e1b5157e21ddb4
出典データセット
uspto-grants-2014_06
特許番号
US08759387B2

反応ノート

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