Methanol → HCID 118383750, compound

HRID 2202704Notes

Reaction equation

HRID 2202704 reaction equation
[OH:1][CH2:2][C@@H:3]1[NH:7][C:6](=[O:8])[C:5](=[C:9]([CH3:11])[CH3:10])[CH2:4]1.CO>CCOC(C)=O.[Pt](=O)=O>[OH:1][CH2:2][C@@H:3]1[NH:7][C:6](=[O:8])[CH:5]([CH:9]([CH3:11])[CH3:10])[CH2:4]1

Participants

5

Reactant 2

HCID 887MethanolHCID 118383396HCID 118383396, compound

Product 1

HCID 118383750HCID 118383750, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of (R)-5-(hydroxymethyl)-3-(propan-2-ylidene)pyrrolidin-2-one (2.223 g, 14.32 mmol) and platinum (iv) oxide (0.325 g, 1.432 mmol) in EtOAc (40 mL)/MeOH (4 mL) at room temperature was stirred in the pressure bottle reactor under H2 (28 psi to 2 psi) overnight. The resulting mixture was filtered through a pad of Celite, washed with EtOAc, and concentrated to give (5R)-5-(hydroxymethyl)-3-isopropylpyrrolidin-2-one (2.251 g, 14.32 mmol, 90% yield) as a light yellow solid. 1H NMR (400 MHz, CDCl3) δ 6.56-6.71 (m, 1H), 3.64-3.80 (m, 2H), 3.37-3.53 (m, 1H), 2.48 (td, J=9.9, 4.5 Hz, 2H), 2.14-2.27 (m, 1H), 1.97-2.13 (m, 1H), 1.50 (ddd, J=12.7, 10.7, 8.3 Hz, 1H), 0.98 (d, J=6.8 Hz, 3H), 0.86 (d, J=6.8 Hz, 3H). m/z (ESI, +ve) 158 (M+H).

Workup

  1. filtrationThe resulting mixture was filtered through a pad of Celite
  2. washwashed with EtOAc
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-590e1a09aed74954bd65b1f28503fd85
Source dataset
uspto-grants-2016_06
Patent number
US09365522B2

Reaction notes

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