Benzyl Bromide → 1-(S)-Benzyloxymethyl-2-(S)-(3-fluorophenyl)-4-methylenecyclopentane

HRID 8778노트

반응식

HRID 8778 반응식
[OH:1][CH2:2][C@@H:3]1[CH2:7][C:6](=[CH2:8])[CH2:5][C@H:4]1[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([F:15])[CH:10]=1.[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[H-].[Na+]>CN(C=O)C.CCOCC>[CH2:16]([O:1][CH2:2][C@H:3]1[CH2:7][C:6](=[CH2:8])[CH2:5][C@@H:4]1[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([F:15])[CH:10]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

참가 물질

6

반응물 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 23548915(+)-trans-1-Hydroxymethyl-4-methylene-2-(3-fluorophenyl)cyclopentane

생성물 1

HCID 235489111-(S)-Benzyloxymethyl-2-(S)-(3-fluorophenyl)-4-methylenecyclopentane수율 90.4%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 6228Dimethylformamide용매

실험 절차

To a solution of (+)-trans-1-hydroxymethyl-4-methylene-2-(3-fluorophenyl)cyclopentane (5.0 g, 26.5 mmol) from Example 1, Step C and benzyl bromide (4.7 mL, 40 mmol) in DMF (130 mL) was added 60% sodium hydride in mineral oil (0.77 g, 32 mmol). The reaction was stirred at room temperature for 24 h was then diluted with ether and slowly quenched into aq. sodium bicarbonate. After three ether extractions, the organic layers were combined, washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by FC (2–5% ethyl acetate in hexanes) to afford the title compound (7.1 g).

후처리

  1. customslowly quenched into aq. sodium bicarbonate
  2. extractionAfter three ether extractions
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by FC (2–5% ethyl acetate in hexanes)

출처 및 근거

ORD 기록
ord-f4f5c73c0baa450b83cabe4ac2020d77
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091211B2

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