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

HRID 587876노트

반응식

HRID 587876 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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%)

후처리

  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

출처 및 근거

ORD 기록
ord-5d5e9374cd434b1498479010135a4a63
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09227930B2

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