Benzyl chloroformate → [5-(tert-Butyl-dimethyl-silanyloxy)-cyclooctyl]-carbamic acid benzyl ester

HRID 2115610노트

반응식

HRID 2115610 반응식
Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].[C:12]([Si:16]([CH3:28])([CH3:27])[O:17][CH:18]1[CH2:25][CH2:24][CH2:23][CH:22]([NH2:26])[CH2:21][CH2:20][CH2:19]1)([CH3:15])([CH3:14])[CH3:13].C(N(C(C)C)CC)(C)C>ClCCl>[CH2:5]([O:4][C:2](=[O:3])[NH:26][CH:22]1[CH2:23][CH2:24][CH2:25][CH:18]([O:17][Si:16]([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:27])[CH3:28])[CH2:19][CH2:20][CH2:21]1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

참가 물질

5

반응물 3

HCID 10387Benzyl chloroformateHCID 81531DiisopropylethylamineHCID 592248345-(tert-Butyl-dimethyl-silanyloxy)-cyclooctylamine

생성물 1

HCID 66656948[5-(tert-Butyl-dimethyl-silanyloxy)-cyclooctyl]-carbamic acid benzyl ester

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Benzyl chloroformate (4 mL, 28.02 mmol) was added to a stirred and cooled (0° C.) solution of the product of Example 5C (14.01 mmol) and diisopropylethyl amine (7.5 mL, 42.03 mmol) in dry dichloromethane (50 mL). After the addition, the solution was warmed to room temperature and stirred for another three hours. It was quenched with NaHCO3 solution. The phases were separated and the organic phase was washed with NaHSO4 solution brine, dried (Na2SO4), filtered, and evaporated. The crude [5-(tert-Butyl-dimethyl-silanyloxy)-cyclooctyl]-carbamic acid benzyl ester was isolated as an oil and was used without further purification. Tetrabutyl ammonium fluoride (42 mL, 1 M in tetrahydrofuran, 42.03 mmol) was added to a solution of crude [5-(tert-Butyl-dimethyl-silanyloxy)-cyclooctyl]-carbamic acid benzyl ester (about 14.01 mmol) in tetrahydrofuran (35 mL). The resulting solution was stirred for two hours at 23° C. before it was partitioned with diethyl ether and water. The organic layer was washed with brine, dried (MgSO4), filtered, and evaporated. The residue was purified over silica gel using 5-50% ethyl acetate in hexanes to give (5-Hydroxy-cyclooctyl)-carbamic acid benzyl ester as an oil. (5-Hydroxy-cyclooctyl)-carbamic acid benzyl ester (2.68 g, 9.66 mmol) was stirred in the presence of Pd(OH)2/C (0.5 g) in methanol under H2 (balloon) for two hours at 23° C. before it was filtered through a pad of Celite and the solvent was evaporated. The title compound was isolated as an oil and used without further purification.

후처리

  1. additionAfter the addition
  2. stirringstirred for another three hours
  3. customIt was quenched with NaHCO3 solution
  4. customThe phases were separated
  5. washthe organic phase was washed with NaHSO4 solution brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. customevaporated

출처 및 근거

ORD 기록
ord-af7a7fc75acb4989bc00ab00a7fd3d2d
출처 데이터셋
uspto-grants-2008_10
특허 번호
US07435833B2

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