Triphenylphosphine → HCID 86708693、化合物

HRID 1430975ノート

反応式

HRID 1430975 の反応式
CC(OC(/N=N/C(OC(C)C)=O)=O)C.[Cl:15][C:16]1[C:23]([N+:24]([O-:26])=[O:25])=[CH:22][C:19]([C:20]#[N:21])=[CH:18][C:17]=1[OH:27].[CH3:28][C:29]1([N:33]2[CH2:38][CH2:37][CH:36](O)[CH2:35][CH2:34]2)[CH2:32][O:31][CH2:30]1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C1COCC1>[Cl:15][C:16]1[C:23]([N+:24]([O-:26])=[O:25])=[CH:22][C:19]([C:20]#[N:21])=[CH:18][C:17]=1[O:27][CH:36]1[CH2:35][CH2:34][N:33]([C:29]2([CH3:28])[CH2:30][O:31][CH2:32]2)[CH2:38][CH2:37]1

参加物

6

反応物 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 23288677HCID 23288677、化合物HCID 86708694HCID 86708694、化合物

生成物 1

HCID 86708693HCID 86708693、化合物収率 66.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

DIAD (0.132 mL, 0.638 mmol) was added to a solution of 4-chloro-3-hydroxy-5-nitrobenzonitrile (95 mg, 0.478 mmol), 1-(3-methyloxetan-3-yl)piperidin-4-ol (78 mg, 0.456 mmol) and triphenylphosphine resin (3 mmol/g loading, 560 mg, 2.136 mmol) in THF (2 mL) and the reaction mixture was stirred at room temperature overnight. The reaction mixture was filtered and the filtrate was concentrated, the crude product was purified by flash chromatography on silica gel using an automated ISCO system (24 g column, eluting with 1-6% 2 N ammonia in methanol/dichloromethane). 4-chloro-3-((1-(3-methyloxetan-3-yl)piperidin-4-yl)oxy)-5-nitrobenzonitrile (106 mg) was obtained as a yellow solid.

後処理

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. customthe crude product was purified by flash chromatography on silica gel using
  4. washan automated ISCO system (24 g column, eluting with 1-6% 2 N ammonia in methanol/dichloromethane)

出典と根拠

ORDレコード
ord-88a286ad7a8a4072af8bdf36e591c4a0
出典データセット
uspto-grants-2015_01
特許番号
US08940736B2

反応ノート

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