Cesium carbonate → 5-(9H-Fluoren-2-yl)-hexahydropyrrolo[3,4-c]pyrrole-2-carboxylic acid tert-butyl ester

HRID 553048

反応式

[C:1]([N:8]1[CH2:15][CH:14]2[CH:10]([CH2:11][NH:12][CH2:13]2)[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].Br[C:17]1[CH:29]=[CH:28][C:27]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH2:20][C:19]=2[CH:18]=1.C([O-])([O-])=O.[Cs+].[Cs+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:4]([O:3][C:1]([N:8]1[CH2:9][CH:10]2[CH:14]([CH2:13][N:12]([C:17]3[CH:29]=[CH:28][C:27]4[C:26]5[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=5)[CH2:20][C:19]=4[CH:18]=3)[CH2:11]2)[CH2:15]1)=[O:2])([CH3:7])([CH3:6])[CH3:5]

参加物

反応条件

温度: 85 °C

実験手順

A mixture of 3-Boc-3,7-diazabicyclo[3.3.0]octane (340 mg, 1.6 mmol; see WO 0181347), 2-bromofluorene (0.47 g, 1.9 mmol), tris(dibenzylideneacetone)dipalladium (0) (Pd2(dba)3; 44 mg, 0.048 mmol; Strem), racemic-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (BINAP; 50 mg, 0.080 mmol; Strem) and Cs2CO3 (1.0 g, 3.2 mmol; Aldrich) in toluene (25 mL) in a sealed tube was warmed to 85° C. and stirred for 18 h. The material was cooled to ambient temperature, filtered, concentrated under reduced pressure and purified by flash chromatography (silica gel, 50% gradient of EtOAc in hexanes) to afford the title compound (350 mg, 0.93 mmol; 58% yield): MS (DCI/NH3) m/z 377 (M+H)+.

後処理

temperatureThe material was cooled to ambient temperature
filtrationfiltered
concentrationconcentrated under reduced pressure
custompurified by flash chromatography (silica gel, 50% gradient of EtOAc in hexanes)

出典と根拠

ORDレコード: ord-7d83b38a47b246ec96fb11935f3c58f2
出典データセット: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US07951791B2

反応式

参加物

反応物 3

生成物 1

試薬・触媒・溶媒 3

反応条件

実験手順

後処理

出典と根拠

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