Triphenylphosphine → Methyl 2-[[1-(tert-butoxycarbonyl)-2-pyrrolidinyl]methoxy]pyridine-5-carboxylate

HRID 350391Notes

Reaction equation

[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([O:10][CH3:11])=[O:9])=[CH:4][N:3]=1.[C:12]([O:16][C:17]([N:19]1[CH2:25][CH2:24][CH2:23][C@H:20]1[CH2:21]O)=[O:18])([CH3:15])([CH3:14])[CH3:13].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:12]([O:16][C:17]([N:19]1[CH2:25][CH2:24][CH2:23][CH:20]1[CH2:21][O:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([O:10][CH3:11])=[O:9])=[CH:4][N:3]=1)=[O:18])([CH3:15])([CH3:13])[CH3:14]

Participants

Conditions

Temperature: 70 °C

Procedure

To a stirred solution of methyl 2-hydroxypyridine-5-carboxylate (1.00 g, 6.529 mmol), N-tert-butoxycarbonylprolinol (1.31 g, 6.529 mmol), and Ph3P (2.06 g, 7.836 mmol) in THF (10 mL) was added DIAD (1.54 mL, 7.836 mmol) at room temp, and the resulting mixture was stirred for 13 hr at 70° C. The mixture was concentrated and the residue was chromatographed on silica-gel with n-hexane:EtOAc (3:1, v/v) as eluent to give 712.3 mg (32%) methyl 2-[[1-(tert-butoxycarbonyl)-2-pyrrolidinyl]methoxy]pyridine-5-carboxylate as a pale yellow oil. 1H-NMR (400 MHz, CDCl3) δ 1.47 (s, 9H), 1.85–1.98 (m, 4H), 3.37 (br s, 2H), 3.92 (s, 3H), 4.12–4.33 (br m, 2H), 4.48 (br s, 1H), 6.75 (m, 1H), 8.15 (m, 1H), 8.79 (m, 1H); MS (FAB) m/z 337 (M++1).

Workup

concentrationThe mixture was concentrated
customthe residue was chromatographed on silica-gel with n-hexane:EtOAc (3:1

Sources & evidence

ORD record: ord-03b3126afaa74ecbb9b9261ac2f4be30
Source dataset: uspto-grants-2007_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07179819B2

Reaction notes

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