Triphenylphosphine → 4-[1-(Tert-butoxycarbonyl)-2-pyrrolidinyl]methoxy-1-iodo-3-methylbenzene

HRID 354299

반응식

HRID 354299 반응식
[I:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([CH3:9])[CH:3]=1.[C:10]([O:14][C:15]([N:17]1[CH2:23][CH2:22][CH2:21][C@H:18]1[CH2:19]O)=[O:16])([CH3:13])([CH3:12])[CH3:11].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[C:10]([O:14][C:15]([N:17]1[CH2:23][CH2:22][CH2:21][CH:18]1[CH2:19][O:8][C:5]1[CH:6]=[CH:7][C:2]([I:1])=[CH:3][C:4]=1[CH3:9])=[O:16])([CH3:13])([CH3:11])[CH3:12]

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 1437134-Iodo-2-methylphenolHCID 643448(S)-(-)-N-Boc-prolinolHCID 5363146Diisopropyl azodicarboxylate

생성물 1

HCID 235124474-[1-(Tert-butoxycarbonyl)-2-pyrrolidinyl]methoxy-1-iodo-3-methylbenzene수율 78%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
70 °C

실험 절차

To a stirred solution of 4-iodo-2-methylphenol (465 mg, 1.987 mmol), N-tert-butoxycarbonylprolinol (400 mg, 1.987 mmol), and Ph3P (625 mg, 2.384 mmol) in THF (7 mL) was added dropwise DIAD (0.5 mL, 2.404 mmol) at room temp, and the mixture was stirred for 13 hr at 70° C. The reaction mixture was concentrated in vacuo and the residue was chromatographed on silica-gel with n-hexane-EtOAc (9:1, v/v) as eluent to give 645.3 mg (78%) 4-[1-(tert-butoxycarbonyl)-2-pyrrolidinyl]methoxy-1-iodo-3-methylbenzene as a pale yellow oil. 1H-NMR (400 MHz, CDCl3) δ1.47 (s, 9H), 1.83-1.89 (m, 1H), 1.96-2.04 (m, 3H), 2.16 (s, 3H), 3.37-3.43 (br m, 2H), 3.81, 3.94 (br m each, 1H), 4.08-4.18 (m, 2H), 6.62 (br s, 1H), 7.42 (s, 2H); MS (FAB) m/z 418 (M++1).

후처리

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue was chromatographed on silica-gel with n-hexane-EtOAc (9:1

출처 및 근거

ORD 기록
ord-237852e4b0de4b2bba8c32fbe85e796c
출처 데이터셋
uspto-grants-2004_06
특허 번호
US06756378B2

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