Cyclobutanone → HCID 86730274, compound

HRID 1850220Notes

Reaction equation

HRID 1850220 reaction equation
[CH:1]([C@H:4]1[CH2:8][O:7][C:6](=[O:9])[N:5]1[C:10]1[CH:15]=[CH:14][N:13]=[C:12]([NH:16][C@H:17]([CH:19]2[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)[CH3:18])[N:11]=1)([CH3:3])[CH3:2].[C:25]1(=O)[CH2:28]C[CH2:26]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C1COCC1>[CH:1]([C@H:4]1[CH2:8][O:7][C:6](=[O:9])[N:5]1[C:10]1[CH:15]=[CH:14][N:13]=[C:12]([NH:16][C@H:17]([CH:19]2[CH2:24][CH2:23][N:22]([CH:25]([CH3:28])[CH3:26])[CH2:21][CH2:20]2)[CH3:18])[N:11]=1)([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 14496CyclobutanoneHCID 5049666Sodium triacetoxyborohydrideHCID 86730270HCID 86730270, compound

Product 1

HCID 86730274HCID 86730274, compoundYield 88.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (S)-4-Isopropyl-3-[2-((S)-1-piperidin-4-yl-ethylamino)-pyrimidin-4-yl]-oxazolidin-2-one (20 mg, 0.060 mmol) in THF (2 mL) was added cyclobutanone (10 mg, 0.17 mmol) and sodium triacetoxyborohydride (20 mg, 0.09 mmol). The reaction was stirred at room temperature for 18 hours. The solvent is then removed under vacuum. The crude material was then purified using reverse phase C18 ODB column water-acetonitrile 0.1% TFA modifier to give (S)-4-Isopropyl-3-{2-[(S)-1-(1-isopropyl-piperidin-4-yl)-ethylamino]-pyrimidin-4-yl}-oxazolidin-2-one (20 mg) in 62% yield.

Workup

  1. customThe solvent is then removed under vacuum
  2. customThe crude material was then purified

Sources & evidence

ORD record
ord-cdf54456ec1c420198657eb446e8ab3b
Source dataset
uspto-grants-2015_02
Patent number
US08957068B2

Reaction notes

Loading…