9-Borabicyclo(3.3.1)nonane → HCID 86722068, 화합물

HRID 1507766노트

반응식

HRID 1507766 반응식
[CH2:1]([O:8][C:9](=[O:15])[NH:10][CH2:11][CH2:12][CH:13]=[CH2:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B1C2CCC[CH:17]1CCC2.[OH-].[Na+].O.Br[C:29]1[CH:34]=[C:33]([C:35]([F:38])([F:37])[F:36])[CH:32]=[CH:31][N:30]=1>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:1]([O:8][C:9](=[O:15])[NH:10][CH:11]([CH3:17])[CH2:12][CH2:13][CH2:14][C:29]1[CH:34]=[C:33]([C:35]([F:38])([F:37])[F:36])[CH:32]=[CH:31][N:30]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

7

반응물 4

HCID 789669-Borabicyclo(3.3.1)nonaneHCID 27815432-Bromo-4-(trifluoromethyl)pyridineHCID 14688338Benzyl but-3-en-1-ylcarbamateHCID 23719242Sodium hydroxide--water (1/1/1)

생성물 1

HCID 86722068HCID 86722068, 화합물수율 99.4%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 1140Toluene용매2회

실험 절차

A solution of but-3-enyl-carbamic acid benzyl ester (3.06 g, 14.0 mmol, 1 eq) in anhydrous toluene (40 mL) was cooled under argon to 0-5° C. 9-BBN (0.50 M, solution in THF; 30.8 mL, 1504 mmol, 1.1 eq.) was added dropwise, the mixture was stirred and allowed to reach room temperature. After 24 h, 1N NaOH/H2O (23.8 mL, 23.8 mmol, 1.7 eq.) was added, followed by 2-bromo-4-trifluoromethyl-pyridine (3.16 g, 14.0 mmol, 1 eq.) and toluene (25 mL). The resulting mixture was degassed and Pd(PPh3)4 (0.89 g, 0.70 mmol, 0.05 eq.) was added. The mixture was rapidly stirred under argon at 60° C. for 24 h, and then it was cooled to room temperature. Afterwards, the mixture was partitioned between EtOAc (100 mL) and brine (100 mL). The organic phase was washed with brine (100 mL), dried over Na2SO4, filtered and concentrated. The crude product was purified by flash chromatography on silica gel (0-50% EtOAc in Heptane) to afford 2 as colorless oil (5.1 g, 99%).

후처리

  1. customto reach room temperature
  2. customThe resulting mixture was degassed
  3. stirringThe mixture was rapidly stirred under argon at 60° C. for 24 h
  4. customAfterwards, the mixture was partitioned between EtOAc (100 mL) and brine (100 mL)
  5. washThe organic phase was washed with brine (100 mL)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude product was purified by flash chromatography on silica gel (0-50% EtOAc in Heptane)

출처 및 근거

ORD 기록
ord-80ee0e8ecea6453ab78169caa620f466
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09221827B2

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