1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 18401884, 화합물

HRID 1018663노트

반응식

HRID 1018663 반응식
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]

참가 물질

7

반응물 4

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 199401P,P-Diphenylphosphinic azideHCID 18401893HCID 18401893, 화합물HCID 86585965HCID 86585965, 화합물

생성물 1

HCID 18401884HCID 18401884, 화합물

시약·촉매·용매 2

HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-65094fee4916495485170592acd0d099
출처 데이터셋
uspto-grants-2002_11
특허 번호
US06482852B2

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