1,8-Diazabicyclo(5.4.0)undec-7-ene → 1-[(1S)-1-azidoethyl]-3-nitrobenzene

HRID 572199ノート

反応式

HRID 572199 の反応式
[N+:1]([C:4]1[CH:5]=[C:6]([C@H:10](O)[CH3:11])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].C1(P([N:27]=[N+:28]=[N-:29])(C2C=CC=CC=2)=O)C=CC=CC=1.N12CCCN=C1CCCCC2>O1CCCC1.C(OCC)(=O)C.O>[N:27]([C@H:10]([C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)[CH3:11])=[N+:28]=[N-:29]

参加物

7

反応物 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 199401P,P-Diphenylphosphinic azideHCID 11147933(R)-1-(3-nitrophenyl)ethanol

生成物 1

HCID 866418551-[(1S)-1-azidoethyl]-3-nitrobenzene収率 130.1%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of (1R)-1-(3-nitrophenyl)ethanol (12 g, 72 mmol) in tetrahydrofuran (220 mL), cooled to 0° C., was added diphenylphosphoryl azide (31 mL, 145 mmol) in one portion followed by 1,8-diazabicyclo[5.4.0]undec-7-ene (22 mL, 145 mmol) dropwise over 30 minutes. The reaction mixture was allowed to warm slowly to room temperature and was stirred for 38 hours after which time the mixture was diluted with ethyl acetate (100 mL) and water (100 mL), the two phases separated and the aqueous phase extracted with ethyl acetate (2×100 mL). The combined organic phases were washed with brine (100 mL), dried (MgSO4) and concentrated under reduced pressure to give a black liquid. The crude liquid was purified by flash chromatography (silica, ethyl acetate/hexanes) to give 1-[(1S)-1-azidoethyl]-3-nitrobenzene (18 g) as a yellow liquid in acceptable purity.

後処理

  1. customthe two phases separated
  2. extractionthe aqueous phase extracted with ethyl acetate (2×100 mL)
  3. washThe combined organic phases were washed with brine (100 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated under reduced pressure
  6. customto give a black liquid
  7. customThe crude liquid was purified by flash chromatography (silica, ethyl acetate/hexanes)

出典と根拠

ORDレコード
ord-6fcb51e3926d484a9945561bbc922c07
出典データセット
uspto-grants-2015_05
特許番号
US09029386B2

反応ノート

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