Allyl bromide → (1R)-benzyl 3-allyl-3-hydroxycyclopentanecarboxylate

HRID 1507666노트

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HRID 1507666 반응식
[O:1]=[C:2]1[CH2:6][CH2:5][C@@H:4]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[CH2:3]1.[Cl-].[NH4+].Br[CH2:20][CH:21]=[CH2:22]>C1COCC1.[Zn]>[CH2:22]([C:2]1([OH:1])[CH2:6][CH2:5][C@@H:4]([C:7]([O:9][CH2:10][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)=[O:8])[CH2:3]1)[CH:21]=[CH2:20]

참가 물질

6

반응물 3

HCID 7841Allyl bromideHCID 25517Ammonium ChlorideHCID 86668857(R)-benzyl 3-oxocyclopentanecarboxylate

생성물 1

HCID 86668862(1R)-benzyl 3-allyl-3-hydroxycyclopentanecarboxylate수율 48.6%

시약·촉매·용매 2

HCID 23994Zinc촉매HCID 8028Tetrahydrofuran용매

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온도
80 °C

실험 절차

To a solution of (R)-benzyl 3-oxocyclopentanecarboxylate (1 g, 4.58 mmol) in THF (10 mL) was added zinc powder (2.098 mL, 229 mmol), saturated aqueous ammonium chloride solution (20 mL) followed by 3-bromoprop-1-ene (1.663 g, 13.75 mmol) slowly at room temperature. The resulting mixture was heated to 80° C. for 3 hours, then allowed to stir at room temperature for additional 12 hours. The reaction mixture was filtered and the filtrate concentrated. To the residue was added ethyl acetate (20 mL) and the resulting mixture was washed with water (5 ml), brine (5 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure to yield (1R)-benzyl 3-allyl-3-hydroxycyclopentanecarboxylate (580 mg, 2.228 mmol, 48.6% yield) as an oil. It was used as such for the next step without further purification. MS (ESI+) m/z 283 (M+Na)+

후처리

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate concentrated
  3. additionTo the residue was added ethyl acetate (20 mL)
  4. washthe resulting mixture was washed with water (5 ml), brine (5 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-73b579cc0c044e71b943e8351ceec1a5
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09221819B2

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