Carbon tetrabromide → 1-(2-(Trimethylsilyl)ethyl) 1'-tert-butyl 5-(bromomethyl)spiro[indoline-3,3'-pyrrolidine]-1,1'-dicarboxylate

HRID 1411310ノート

反応式

HRID 1411310 の反応式
O[CH2:2][C:3]1[CH:4]=[C:5]2[C:11]3([CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12]3)[CH2:10][N:9]([C:23]([O:25][CH2:26][CH2:27][Si:28]([CH3:31])([CH3:30])[CH3:29])=[O:24])[C:6]2=[CH:7][CH:8]=1.C(Br)(Br)(Br)[Br:33].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[Br:33][CH2:2][C:3]1[CH:4]=[C:5]2[C:11]3([CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12]3)[CH2:10][N:9]([C:23]([O:25][CH2:26][CH2:27][Si:28]([CH3:31])([CH3:30])[CH3:29])=[O:24])[C:6]2=[CH:7][CH:8]=1

参加物

5

反応物 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 904495331-(2-(Trimethylsilyl)ethyl) 1'-tert-butyl 5-(hydroxymethyl)spiro[indoline-3,3'-pyrrolidine]-1,1'-dicarboxylate

生成物 1

HCID 904495541-(2-(Trimethylsilyl)ethyl) 1'-tert-butyl 5-(bromomethyl)spiro[indoline-3,3'-pyrrolidine]-1,1'-dicarboxylate収率 77.8%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

1-(2-(Trimethylsilyl)ethyl) 1′-tert-butyl 5-(hydroxymethyl)spiro[indoline-3,3′-pyrrolidine]-1,1′-dicarboxylate (441 mg, 0.98 mmol) was dissolved in methylene chloride (10 mL). Thereafter, carbon tetrabromide (359 mg, 1.08 mmol) and triphenylphosphine (310 mg, 1.18 mmol) were added to the above obtained solution under cooling on ice, and the thus obtained mixture was then stirred at the same temperature as above for 2.5 hours. Thereafter, the reaction solution was concentrated in vacuo, and the obtained residue was then purified by silica gel column chromatography (hexane:ethyl acetate=10:1) to obtain 1-(2-(trimethylsilyl)ethyl) 1′-tert-butyl 5-(bromomethyl)spiro[indoline-3,3′-pyrrolidine]-1,1′-dicarboxylate (390 mg, 77%) in the form of a colorless amorphous product.

後処理

  1. temperatureunder cooling on ice
  2. concentrationThereafter, the reaction solution was concentrated in vacuo
  3. customthe obtained residue was then purified by silica gel column chromatography (hexane:ethyl acetate=10:1)

出典と根拠

ORDレコード
ord-ed837e15572a40ab8d665eb9e5b76ee4
出典データセット
uspto-grants-2014_12
特許番号
US08921576B2

反応ノート

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