Water → HCID 59557382, compound

HRID 389343Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:10]#[N:11])[CH:6]=[CH:7][CH:8]=1.[CH2:18]([N:25]1[CH2:29][CH2:28][C@H:27](OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:26]1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.CC(C)([O-])C.[K+].O>C1COCC1>[CH2:18]([N:25]1[CH2:29][CH2:28][C@@H:27]([C:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=2)([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:10]#[N:11])[CH2:26]1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a stirred solution of (3-methoxyphenyl)phenylacetonitrile (5.2 g, 23 mmol; prepared as described in Preparation 6) in THF (100 mL) was added toluene-4-sulfonic acid (S)-1-benzylpyrrolidin-3-yl ester (7.2 g, 22 mmol), followed by the addition of potassium t-butoxide (4.0 g, 36 mmol). The mixture was heated to 80° C. for 1 hour, then allowed to cool and H2O (10 mL) was added. The mixture was filtered through a pad of Celite®. The mixture was washed with a saturated aqueous NaCl solution (100 mL) and the organic phase was separated, dried over MgSO4, and filtered. The solvent was removed under reduced pressure. The crude material was purified via silica gel chromatography to afford the title compound (6.2 g, 17 mmol). MS m/z: {M+H+] calcd for C26H26N2O, 382.5. found 383.4.

Workup

temperatureto cool
filtrationThe mixture was filtered through a pad of Celite®
washThe mixture was washed with a saturated aqueous NaCl solution (100 mL)
customthe organic phase was separated
dry with materialdried over MgSO4
filtrationfiltered
customThe solvent was removed under reduced pressure
customThe crude material was purified via silica gel chromatography

Sources & evidence

ORD record: ord-e8705f03412341b0be525691935f88d0
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08378121B2

Reaction notes

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