1,8-Diazabicyclo(5.4.0)undec-7-ene → 4(R)-Azido-6,8-dibromo-chroman

HRID 1008959ノート

反応式

HRID 1008959 の反応式
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([Br:12])[CH:11]=1)[O:8][CH2:7][CH2:6][C@@H:5]2O.C1(P([N:28]=[N+:29]=[N-:30])(C2C=CC=CC=2)=O)C=CC=CC=1.N12CCCN=C1CCCCC2>O1CCCC1.C(OC(=O)C)C>[N:28]([C@H:5]1[C:4]2[C:9](=[C:10]([Br:12])[CH:11]=[C:2]([Br:1])[CH:3]=2)[O:8][CH2:7][CH2:6]1)=[N+:29]=[N-:30]

参加物

6

反応物 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 199401P,P-Diphenylphosphinic azideHCID 67304261(S)-6,8-Dibromochroman-4-ol

生成物 1

HCID 866200164(R)-Azido-6,8-dibromo-chroman

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A solution containing 6,8-dibromo-chroman-4(S)-ol in tetrahydrofuran (0.17M) and 1.2 equivalents of diphenylphosphorylazide was stirred for 15 minutes at room temperature. The solution was cooled to 10° C. and 2.5 equivalents of 1,8-diazabicyclo[5.4.0]undec-7-ene added. The mixture was stirred with gradual warming to room temperature and maintained for 48 h. The mixture was diluted with ethylacetate and washed with brine followed by water. The organic phase was concentrated to afford the title compound as a tan oil.

後処理

  1. temperatureThe solution was cooled to 10° C.
  2. stirringThe mixture was stirred
  3. temperaturewith gradual warming to room temperature
  4. temperaturemaintained for 48 h
  5. washwashed with brine
  6. concentrationThe organic phase was concentrated

出典と根拠

ORDレコード
ord-a7dbc9ef49184c28889d6fa51a957303
出典データセット
uspto-grants-2011_07
特許番号
US07973050B2

反応ノート

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