1,8-Diazabicyclo(5.4.0)undec-7-ene → (R)-1-azido-5-bromo-indane

HRID 1913402ノート

反応式

HRID 1913402 の反応式
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C@@H:7](O)[CH2:6][CH2:5]2.C1C=CC(OP(OC2C=CC=CC=2)([N:21]=[N+:22]=[N-:23])=O)=CC=1.N12CCCN=C1CCCCC2>C1(C)C=CC=CC=1.CCOC(C)=O>[N:21]([C@H:7]1[C:8]2[C:4](=[CH:3][C:2]([Br:1])=[CH:10][CH:9]=2)[CH2:5][CH2:6]1)=[N+:22]=[N-:23]

参加物

6

反応物 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 123414Diphenylphosphoryl azideHCID 29414737(1S)-5-bromo-2,3-dihydro-1H-inden-1-ol

生成物 1

HCID 59179602(R)-1-azido-5-bromo-indane収率 83.5%

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
15 °C

実験手順

A solution of (S)-5-bromo-indan-1-ol (15.0 g, 70.4 mmol) in toluene (150 mL) was cooled in an ice bath under N2 and was treated with diphenylphosphoric azide (DPPA, 22.0 g, 91.5 mmol) in one portion followed by 1,8-diazabicyclo[5,4,0]undec-7-ene (15.0 g, 98.6 mmol). The reaction temperature was kept between 3 and 10° C. during 3 hours of addition and the mixture was warmed to 15° C. over the next hour (TLC indicated no starting material). The mixture was diluted with EtOAc (300 mL) and was washed with water. The organic layer was dried over Na2SO4, filtered and concentrated to give a dark oil. The crude product was purified by silica gel column (packed with 1% Et3N in hexanes, hexane eluant) to give (R)-1-azido-5-bromo-indane (14 g, 83%) as an oil which was used directly in the next step.

後処理

  1. additionThe reaction temperature was kept between 3 and 10° C. during 3 hours of addition
  2. washwas washed with water
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a dark oil
  7. customThe crude product was purified by silica gel column (packed with 1% Et3N in hexanes, hexane eluant)

出典と根拠

ORDレコード
ord-72eacf37d2454f4ba447640a285f3583
出典データセット
uspto-grants-2013_12
特許番号
US08609680B2

反応ノート

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