1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 18401884、化合物

HRID 1018663ノート

反応式

HRID 1018663 の反応式
C1(COC2C=CC3C(O)CCCCC=3C=2)CCCCC1.C1CCN2C(=NCCC2)CC1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.[N:49]([CH:52]1[C:58]2[CH:59]=[CH:60][C:61]([O:63][CH2:64][CH:65]3[CH2:70][CH2:69][CH2:68][CH2:67][CH2:66]3)=[CH:62][C:57]=2[CH2:56][CH2:55][CH2:54][CH2:53]1)=[N+:50]=[N-:51].C1(COC2C=CC3C=CCCCC=3C=2)CCCCC1>C1(C)C=CC=CC=1.CCOC(C)=O>[N:49]([CH:52]1[C:58]2[CH:59]=[CH:60][C:61]([O:63][CH2:64][CH:65]3[CH2:70][CH2:69][CH2:68][CH2:67][CH2:66]3)=[CH:62][C:57]=2[CH2:56][CH2:55][CH2:54][CH2:53]1)=[N+:50]=[N-:51]

参加物

7

反応物 4

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 199401P,P-Diphenylphosphinic azideHCID 18401893HCID 18401893、化合物HCID 86585965HCID 86585965、化合物

生成物 1

HCID 18401884HCID 18401884、化合物

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To 2-cyclohexylmethoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-ol (14.2 g, 52.0 mmol) in toluene (100 mL) at 0° C. was added DBU (9.4 mL, 62.9 mmol) followed by diphenylphosphoryl azide (13.6 mL, 62.9 mmol). The mixture was allowed to stir for 18 h at rt, diluted with EtOAc, then washed successively with 1 N HCl, and water. The organic layer was dried over MgSO4, filtered, concentrated, and chomatographed over silica gel (5% EtOAc/hexane) to yield a 7:3 mixture of 5-azido-2-cyclohexylmethoxy-6,7,8,9-tetrahydro-5H-benzocycloheptene/3-cyclohexylmethoxy-6,7-dihydro-5H-benzocycloheptene (12.6 g). This mixture was used without further purification in the next reaction.

後処理

  1. washwashed successively with 1 N HCl, and water
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto yield
  6. customThis mixture was used without further purification in the next reaction

出典と根拠

ORDレコード
ord-65094fee4916495485170592acd0d099
出典データセット
uspto-grants-2002_11
特許番号
US06482852B2

反応ノート

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