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

HRID 1811653
ノート
印刷プレビュー

反応式

HRID 1811653 の反応式
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
参加物実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran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=4:1→0:1) to obtain 24.3 g of benzyl(R)-3-[(R)-1-(naphthalen-1-yl)ethylamino]piperidine-1-carboxylate.

後処理

  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)

出典と根拠

ORDレコード
ord-0b5dc2227fa649b4907f32531be23ea6
出典データセット
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08362274B2

反応ノート

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