Tributylphosphine → Ethyl 3-(4-{[(1S)-1-(6-bromo-2-pyridinyl)pentyl]oxy}-2-methylphenyl)propanoate

HRID 1391778

반응식

HRID 1391778 반응식
[Br:1][C:2]1[N:7]=[C:6]([C@H:8]([OH:13])[CH2:9][CH2:10][CH2:11][CH3:12])[CH:5]=[CH:4][CH:3]=1.O[C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])=[C:17]([CH3:28])[CH:16]=1.C1CCN(C(N=NC(N2CCCCC2)=O)=O)CC1.CCCCP(CCCC)CCCC>C1COCC1>[Br:1][C:2]1[N:7]=[C:6]([C@@H:8]([O:13][C:15]2[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])=[C:17]([CH3:28])[CH:16]=2)[CH2:9][CH2:10][CH2:11][CH3:12])[CH:5]=[CH:4][CH:3]=1

참가 물질

6

반응물 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 21986481Ethyl 3-(4-hydroxy-2-methylphenyl)propanoateHCID 86604659(1R)-1-(6-Bromo-2-pyridinyl)-1-pentanol

생성물 1

HCID 58629903Ethyl 3-(4-{[(1S)-1-(6-bromo-2-pyridinyl)pentyl]oxy}-2-methylphenyl)propanoate수율 75.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a stirring solution of (1R)-1-(6-bromo-2-pyridinyl)-1-pentanol (261 mg, 1.07 mmol) and ethyl 3-(4-hydroxy-2-methylphenyl)propanoate (329 mg, 1.58 mmol) in THF (13 mL) at 0° C. under nitrogen was added ADDP (531 mg, 2.10 mmol) followed by tri-N-butylphosphine (0.525 mL, 2.10 mmol) drop-wise. The resulting mixture was then stirred with slow warming to ambient temperature over 15 h. The reaction mixture was then concentrated under vaccum and the solid residue purified directly by SPE (silica, 10 g cartridge) with a pad of celite on the top, eluting with cyclohexane:EtOAc (gradient 100:1 to 20:1) to afford the title compound (350 mg).

후처리

  1. concentrationThe reaction mixture was then concentrated under vaccum
  2. customthe solid residue purified directly by SPE (silica, 10 g cartridge) with a pad of celite on the top
  3. washeluting with cyclohexane

출처 및 근거

ORD 기록
ord-8d68972fb3fb4690a8df30f74b29f2da
출처 데이터셋
uspto-grants-2008_03
특허 번호
US07338960B2

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