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

HRID 350359Notes

Reaction equation

[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]

Participants

Conditions

Temperature: 70 °C

Procedure

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) δ 1.47 (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).

Workup

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

Sources & evidence

ORD record: ord-821887884bf14a30af962a1d847349d7
Source dataset: uspto-grants-2007_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07179819B2

Reaction notes

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