Boron tribromide → ethyl 1-benzyl-6-hydroxy-2,3-dihydro-1H-inden-2-ylcarbamate

HRID 587876ノート

反応式

HRID 587876 の反応式
[CH2:1]([CH:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:17]C)[CH:15]=2)[CH2:10][CH:9]1[NH:19][C:20](=[O:24])[O:21][CH2:22][CH3:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.BrB(Br)Br>ClCCl>[CH2:1]([CH:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([OH:17])[CH:15]=2)[CH2:10][CH:9]1[NH:19][C:20](=[O:24])[O:21][CH2:22][CH3:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

4

反応物 2

HCID 25134Boron tribromideHCID 66740684ethyl 1-benzyl-6-methoxy-2,3-dihydro-1H-inden-2-ylcarbamate

生成物 1

HCID 66740125ethyl 1-benzyl-6-hydroxy-2,3-dihydro-1H-inden-2-ylcarbamate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a stirred and cooled (−10° C.) solution of ethyl 1-benzyl-6-methoxy-2,3-dihydro-1H-inden-2-ylcarbamate (668 mg, 2.053 mmol) in dichloromethane (15 ml) under argon was added dropwise 1M tribromoborane (6.16 ml, 6.16 mmol) and stirred over night while the reaction mixture was allowed to warm up to room temperature. Poured into ice water, diluted with dichloromethane, separated organic layer and the aqueous layer was extracted twice with dichloromethane. The combined organic layers were washed subsequently with water, sodium bicarbonate and brine, dried, filtered and evaporated to obtain ethyl 1-benzyl-6-hydroxy-2,3-dihydro-1H-inden-2-ylcarbamate as a brown solid. m=620 mg (97%)

後処理

  1. stirringstirred over night while the reaction mixture
  2. customseparated organic layer
  3. extractionthe aqueous layer was extracted twice with dichloromethane
  4. washThe combined organic layers were washed subsequently with water, sodium bicarbonate and brine
  5. customdried
  6. filtrationfiltered
  7. customevaporated

出典と根拠

ORDレコード
ord-5d5e9374cd434b1498479010135a4a63
出典データセット
uspto-grants-2016_01
特許番号
US09227930B2

反応ノート

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