Diisopropylethylamine → HCID 71212278, compound

HRID 1752244Notes

Reaction equation

HRID 1752244 reaction equation
[O:1]=[C:2]1[C@@H:6](OS(C)(=O)=O)[CH2:5][CH2:4][NH:3]1.[CH3:12][O:13][C:14]1[CH:15]=[C:16]2[C:25](=[CH:26][CH:27]=1)[C:24](=[O:28])[C:18]1([CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1)[CH2:17]2.CCN(C(C)C)C(C)C>C(#N)C>[CH3:12][O:13][C:14]1[CH:15]=[C:16]2[C:25](=[CH:26][CH:27]=1)[C:24](=[O:28])[C:18]1([CH2:23][CH2:22][N:21]([CH:6]3[CH2:5][CH2:4][NH:3][C:2]3=[O:1])[CH2:20][CH2:19]1)[CH2:17]2

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 14256265(S)-2-oxopyrrolidin-3-yl methanesulfonateHCID 71212150HCID 71212150, compound

Product 1

HCID 71212278HCID 71212278, compoundYield 77.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
85 °C

Procedure

To a 250 mL round bottom flask was added methanesulfonic acid (S)-2-oxo-pyrrolidin-3-yl ester (2) (4.76 mmol, 852 mg) and 5-methoxyspiro[indene-2,4′-piperidin]-1(3H)-one (3) (4.32 mmol, 1.00 g) in DIEA (17.29 mmol, 3.02 mL) and acetonitrile (20 mL). The solution was then heated to 85° C. for 90 min. The reaction was concentrated in vacuo and flash column chromatography (silica) was performed eluting with ethyl acetate to 20% MeOH/ethyl acetate afforded the title compound (1.05 g, 77% yield). Calculated MS=306.2. found MS (ESI) m/e 307.3 (M+H+); HPLC (Novapak 150×3.9 mm C18 column: mobile phase: 10-90% acetonitrile/water with 0.1% TFA, at 2 mL/min over 5 min.) retention time=2.253 min.

Workup

  1. concentrationThe reaction was concentrated in vacuo and flash column chromatography (silica)
  2. washwas performed eluting with ethyl acetate to 20% MeOH/ethyl acetate

Sources & evidence

ORD record
ord-25e6ac8ad6e441debc0efbe01149da71
Source dataset
uspto-grants-2015_10
Patent number
US09163003B2

Reaction notes

Loading…