Triphenylphosphine → HCID 11404273, compound

HRID 1003262Notes

Reaction equation

N(C(OCC)=O)=NC(OCC)=O.[C:13]([O:17][C:18]([N:20]1[CH2:25][CH2:24][CH2:23][C@:22](/[CH:27]=[CH:28]\[CH2:29]O)([OH:26])[C@@H:21]1[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:19])([CH3:16])([CH3:15])[CH3:14].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[C:13]([O:17][C:18]([N:20]1[CH2:25][CH2:24][CH2:23][C@:22]2([O:26][CH2:29][CH:28]=[CH:27]2)[C@@H:21]1[C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)=[O:19])([CH3:14])([CH3:15])[CH3:16]

Participants

Conditions

Temperature: 0 °C

Procedure

Diethyl azodicarboxylate (18.2 ml, 115 mmol) in THF (100 ml) was added dropwise to a solution of Z-(2S,3R)-1-tert-butoxycarbonyl-3-(3-hydroxyprop-1-en-1-yl)-2-phenylpiperidin-3-ol (Description 20; 32 g, 96 mmol) and triphenylphosphine (30.2 g, 115 mmol) in THF (700 ml). The mixture was stirred at 0° C. for 30 minutes then at room temperature for 1.5 hours. The solvent was evaporated under reduced pressure and the residue was purified by flash column chromatography on silica gel, eluting with hexane/ethyl acetate (95:5 increasing to 80:20) to give the title compound as a colorless solid (23.4 g, 77%). MS (ES+) m/z 316 (M+ +1, 100%). 1H NMR (CDCl3) δ 7.45 (2H, d, J 7.4 Hz), 7.27 (2H, t, J 7.4 Hz), 7.20 (1H, t, J 7.4 Hz), 6.03 (1H, dt, J 6.1, 2.0 Hz), 5.68 (1H, dt, J 6.1, 2.0 Hz), 5.06 (1H, s), 4.61 (1H, dt, J 13.1, 2.0 Hz), 4.32 (1H, dt, J 13.1, 2.0 Hz), 4.08 (1H, m), 3.05 (1H, m), 2.05 (1H, m), 1.75 (3H, m), and 1.37 (9H, s).

Workup

waitat room temperature for 1.5 hours
customThe solvent was evaporated under reduced pressure
customthe residue was purified by flash column chromatography on silica gel
washeluting with hexane/ethyl acetate (95:5 increasing to 80:20)

Sources & evidence

ORD record: ord-6fa78d579bd6410585686956f324e2f8
Source dataset: uspto-grants-2000_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06046195

Reaction notes

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