1-(3-Nitro-7,8-dihydro-6H-5-oxa-9-aza-benzocyclohepten-9-yl)-2-pyrrolidin-1-yl-ethanone → 3-Nitro-9-(2-pyrrolidin-1-yl-ethyl)-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocycloheptene

HRID 1041690노트

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HRID 1041690 반응식
[N+:1]([C:4]1[CH:22]=[CH:21][C:7]2[N:8]([C:13](=O)[CH2:14][N:15]3[CH2:19][CH2:18][CH2:17][CH2:16]3)[CH2:9][CH2:10][CH2:11][O:12][C:6]=2[CH:5]=1)([O-:3])=[O:2]>O1CCCC1>[N+:1]([C:4]1[CH:22]=[CH:21][C:7]2[N:8]([CH2:13][CH2:14][N:15]3[CH2:19][CH2:18][CH2:17][CH2:16]3)[CH2:9][CH2:10][CH2:11][O:12][C:6]=2[CH:5]=1)([O-:3])=[O:2]

참가 물질

3

반응물 1

HCID 672641431-(3-Nitro-7,8-dihydro-6H-5-oxa-9-aza-benzocyclohepten-9-yl)-2-pyrrolidin-1-yl-ethanone

생성물 1

HCID 672645583-Nitro-9-(2-pyrrolidin-1-yl-ethyl)-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocycloheptene수율 70.7%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
60 °C

실험 절차

1.00 M of Borane-THF complex in Tetrahydrofuran (10.0 mL; Acros) was added to 1-(3-Nitro-7,8-dihydro-6H-5-oxa-9-aza-benzocyclohepten-9-yl)-2-pyrrolidin-1-yl-ethanone (0.401 g, 1.31 mmol) in Tetrahydrofuran (10 mL). The mixture was heated at 60° C. under an atmosphere of Nitrogen. overnight. The mixture was quenched with 1N HCl (5 mL) and stirred for 1 h at 60° C. The solution was neutralized by pouring into satd. sodium bicarbonate and extracted with DCM (3×). The extract was dried and conc. in vacuo to give 3-Nitro-9-(2-pyrrolidin-1-yl-ethyl)-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocycloheptene as an oil (270 mg, 70%).

후처리

  1. customovernight
  2. customThe mixture was quenched with 1N HCl (5 mL)
  3. additionby pouring into satd
  4. extractionsodium bicarbonate and extracted with DCM (3×)
  5. customThe extract was dried and conc. in vacuo

출처 및 근거

ORD 기록
ord-a2d181e16ecf4e8c8e66bbcb4686e2c9
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08552186B2

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