Triphenylphosphine → Triphenylphosphine

HRID 858927ノート

反応式

HRID 858927 の反応式
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][OH:6].[C:10]1([P:16]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[CH3:29][O:30][C:31]([C@H:33]1[CH2:37][C:36](=[O:38])[N:35]([C:39]2[CH:44]=[CH:43][C:42](O)=[CH:41][CH:40]=2)[CH2:34]1)=[O:32].[N:46]([C:54]([O:56][CH:57]([CH3:59])[CH3:58])=[O:55])=[N:47][C:48]([O:50][CH:51]([CH3:53])[CH3:52])=[O:49].C1(P(=O)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[CH3:29][O:30][C:31]([C@H:33]1[CH2:37][C:36](=[O:38])[N:35]([C:39]2[CH:44]=[CH:43][C:42]([O:6][CH2:5][C:4]3[CH:7]=[CH:8][CH:9]=[C:2]([F:1])[CH:3]=3)=[CH:41][CH:40]=2)[CH2:34]1)=[O:32].[C:23]1([P:16]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1.[NH:46]([C:54]([O:56][CH:57]([CH3:59])[CH3:58])=[O:55])[NH:47][C:48]([O:50][CH:51]([CH3:52])[CH3:53])=[O:49]

参加物

9

反応物 5

HCID 11776TriphenylphosphineHCID 13097Triphenylphosphine OxideHCID 680083-Fluorobenzylic alcoholHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 785701HCID 785701、化合物

生成物 3

HCID 11776TriphenylphosphineHCID 88220Diisopropyl bicarbamateHCID 68614551(S)-1-[4-(3-fluoro-benzyloxy)-phenyl]-5-oxo-pyrrolidine-3-carboxylic acid methyl ester

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A solution of 110.6 mmol of 3-fluoro-benzylalcohol and 108.8 mmol of triphenylphosphine in 150 ml of tetrahydrofuran was added dropwise, within 50 min under a nitrogen atmosphere at 0° C., to a solution of 100.5 mmol of (S)-1-(4-hydroxy-phenyl)-5-oxo-pyrrolidine-3-carboxylic acid methyl ester and 100.5 mmol of diisopropyl azodicarboxylate in 200 ml of tetrahydrofuran. The mixture was left to warm to RT and stirring was continued for 18 hours. The mixture was evaporated under reduced pressure. The solid residue was triturated in 400 ml of ether to leave a white solid mainly consisting of the product and triphenylphosphinoxide. After filtration, the solid material was triturated in 100 ml of cold methanol to yield (S)-1-[4-(3-fluoro-benzyloxy)-phenyl]-5-oxo-pyrrolidine-3-carboxylic acid methyl ester as a white solid [MS: m/e=344 (M+H)+] together with traces of triphenylphosphine and diisopropyl hydrazodicarboxylate.

後処理

  1. waitThe mixture was left
  2. customThe mixture was evaporated under reduced pressure
  3. customThe solid residue was triturated in 400 ml of ether
  4. customto leave a white solid
  5. filtrationAfter filtration
  6. customthe solid material was triturated in 100 ml of cold methanol

出典と根拠

ORDレコード
ord-052cf91d6ead4b40a5385415d5ed7399
出典データセット
uspto-grants-2006_12
特許番号
US07148362B2

反応ノート

読み込み中…