Triphenylphosphine → Triphenylphosphine

HRID 858927노트

반응식

HRID 858927 반응식
[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]

참가 물질

9

반응물 5

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

생성물 3

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-052cf91d6ead4b40a5385415d5ed7399
출처 데이터셋
uspto-grants-2006_12
특허 번호
US07148362B2

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