Phthalimide → (R)-tert-butyl 3-((R)-1-(3-chlorophenyl)-1-(2-(1,3-dioxoisoindolin-2-yl)ethoxy)ethyl)piperidine-1-carboxylate

HRID 451716

反応式

HRID 451716 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([C@@:8]([C@@H:14]2[CH2:19][CH2:18][CH2:17][N:16]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:15]2)([O:10][CH2:11][CH2:12]O)[CH3:9])[CH:5]=[CH:6][CH:7]=1.[C:27]1(=[O:37])[NH:31][C:30](=[O:32])[C:29]2=[CH:33][CH:34]=[CH:35][CH:36]=[C:28]12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C@@:8]([C@@H:14]2[CH2:19][CH2:18][CH2:17][N:16]([C:20]([O:22][C:23]([CH3:24])([CH3:26])[CH3:25])=[O:21])[CH2:15]2)([O:10][CH2:11][CH2:12][N:31]2[C:27](=[O:37])[C:28]3[C:29](=[CH:33][CH:34]=[CH:35][CH:36]=3)[C:30]2=[O:32])[CH3:9])[CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 59201466(R)-tert-butyl 3-((R)-1-(3-chlorophenyl)-1-(2-hydroxyethoxy)ethyl)piperidine-1-carboxylate

生成物 1

HCID 59201660(R)-tert-butyl 3-((R)-1-(3-chlorophenyl)-1-(2-(1,3-dioxoisoindolin-2-yl)ethoxy)ethyl)piperidine-1-carboxylate収率 51%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A mixture of (R)-tert-butyl 3-((R)-1-(3-chlorophenyl)-1-(2-hydroxyethoxy)ethyl)piperidine-1-carboxylate (1.000 g, 2.6 mmol), phthalimide (1.490 g, 10.1 mmol), triphenylphosphine (4.130 g, 15.7 mmol), and DIAD (3.430 g, 17.0 mmol) in THF was stirred at rt for 40 h. After the reaction mixture was evaporated under reduced pressure, the crude product was purified by reversed-phase HPLC to afford 0.6792 g (51%) of (R)-tert-butyl 3-((R)-1-(3-chlorophenyl)-1-(2-(1,3-dioxoisoindolin-2-yl)ethoxy)ethyl)piperidine-1-carboxylate. MS ESI +ve m/z 537 (M+Na).

後処理

  1. customAfter the reaction mixture was evaporated under reduced pressure
  2. customthe crude product was purified by reversed-phase HPLC

出典と根拠

ORDレコード
ord-9555b888116442d585495bf6952c7c3a
出典データセット
uspto-grants-2013_07
特許番号
US08487108B2

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