Cyclobutanone → HCID 86730273, compound

HRID 1850219Notes

Reaction equation

HRID 1850219 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][CH2:27][CH2:26]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C1COCC1>[CH:25]1([N:22]2[CH2:23][CH2:24][CH:19]([C@@H:17]([NH:16][C:12]3[N:11]=[C:10]([N:5]4[C@@H:4]([CH:1]([CH3:2])[CH3:3])[CH2:8][O:7][C:6]4=[O:9])[CH:15]=[CH:14][N:13]=3)[CH3:18])[CH2:20][CH2:21]2)[CH2:28][CH2:27][CH2:26]1

Participants

5

Reactant 3

HCID 14496CyclobutanoneHCID 5049666Sodium triacetoxyborohydrideHCID 86730270HCID 86730270, compound

Product 1

HCID 86730273HCID 86730273, compoundYield 62%

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 (28 mg, 0.084 mmol) in THF (2 mL) was added cyclobutanone (14 mg, 0.20 mmol) and sodium triacetoxyborohydride (28 mg, 0.13 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)-3-{2-[(S)-1-(1-Cyclobutyl-piperidin-4-yl)-ethylamino]-pyrimidin-4-yl}-4-isopropyl-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-cbf01118e4f74cb1bb9173a64b554b0b
Source dataset
uspto-grants-2015_02
Patent number
US08957068B2

Reaction notes

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