p-Toluenesulfonic acid monohydrate → HCID 118383396, compound

HRID 2202703Notes

Reaction equation

HRID 2202703 reaction equation
CC1(C)[N:6]2[C:7](=[O:13])[C:8](=[C:10]([CH3:12])[CH3:11])[CH2:9][C@@H:5]2[CH2:4][O:3]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[OH:3][CH2:4][C@@H:5]1[NH:6][C:7](=[O:13])[C:8](=[C:10]([CH3:12])[CH3:11])[CH2:9]1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 118383472HCID 118383472, compound

Product 1

HCID 118383396HCID 118383396, compoundYield 60.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of (R)-3,3-dimethyl-6-(propan-2-ylidene)tetrahydropyrrolo[1,2-c]oxazol-5(3H)-one (4.63 g, 23.73 mmol) in MeOH (50 mL) at room temperature was added p-toluenesulfonic acid monohydrate (0.451 g, 2.373 mmol) and then heated at 60° C. for 45 min. The solvent was evaporated and the crude material was absorbed onto a plug of silica gel and was purified by chromatography through a REDISEP™ pre-packed silica gel column (80 g), eluting with a gradient of 0% to 10% MeOH in DCM to give (R)-5-(hydroxymethyl)-3-(propan-2-ylidene)pyrrolidin-2-one (2.223 g, 14.32 mmol, 60.4% yield) as an yellow solid. 1H NMR (400 MHz, CDCl3) δ 6.60 (br. s., 1H), 3.74 (td, J=8.0, 3.9 Hz, 1H), 3.67 (dd, J=11.1, 3.6 Hz, 1H), 3.44 (dd, J=11.1, 7.3 Hz, 1H), 2.75-2.86 (m, 1H), 2.81 (dd, J=16.5, 8.7 Hz, 1H), 2.33-2.43 (m, 1H), 2.23 (s, 3H), 1.77 (s, 3H). m/z (ESI, +ve) 156 (M+H).

Workup

  1. customThe solvent was evaporated
  2. customthe crude material was absorbed onto a plug of silica gel
  3. customwas purified by chromatography through a REDISEP™ pre-packed silica gel column (80 g)
  4. washeluting with a gradient of 0% to 10% MeOH in DCM

Sources & evidence

ORD record
ord-46db25811f114810ab964fbc2d61ed2a
Source dataset
uspto-grants-2016_06
Patent number
US09365522B2

Reaction notes

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