Ozone → HCID 42642289, compound

HRID 403590Notes

Reaction equation

HRID 403590 reaction equation
[CH2:1]([C@:4]1([C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)[CH2:9][CH2:8][N:7]([C@H:10]([C:12]([CH3:15])([CH3:14])[CH3:13])[CH3:11])[C:6](=[O:16])[NH:5]1)[CH:2]=C.[O:24]=[O+][O-].[BH4-].[Na+]>C(Cl)Cl>[CH3:13][C:12]([CH3:15])([CH3:14])[C@@H:10]([N:7]1[CH2:8][CH2:9][C@@:4]([C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)([CH2:1][CH2:2][OH:24])[NH:5][C:6]1=[O:16])[CH3:11]

Participants

5

Reactant 3

HCID 24823OzoneHCID 4311764Sodium borohydrideHCID 58485258HCID 58485258, compound

Product 1

HCID 42642289HCID 42642289, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (R)-4-allyl-1-((S)-3,3-dimethylbutan-2-yl)-4-(4-fluorophenyl)tetrahydropyrimidin-2(1H)-one (285 mg, 0.90 mmol) in CH2Cl2 (5 mL) was treated with O3 till the mixture was turned blue. Then NaBH4 was added and the mixture was stirred at rt till the reaction was over. The reaction was quenched with H2O, and the mixture was extracted with EtOAc. The organic phase was washed with brine, dried over Na2SO4, filtered and concentrated to give the crude product, which was purified by preparative TLC to afford (S)-1-((S)-3,3-dimethylbutan-2-yl)-4-(4-fluorophenyl)-4-(2-hydroxyethyl)tetrahydropyrimidin-2(1H)-one (120 mg, 42%). LC-MS Method 1 tR=1.021, min, m/z=323.1; 1H NMR (CDCl3): 0.72 (s, 9H), 0.99 (d, 3H), 1.35-1.98 (m, 2H), 2.03-2.14 (m, 3H), 2.51 (m, 1H), 3.04 (m, 1H), 3.31 (m, 1H), 3.64 (m, 1H), 4.47 (m, 1H), 6.66 (s, 1H), 6.96-7.01 (m, 2H), 7.24-7.28 (m, 2H).

Workup

  1. customThe reaction was quenched with H2O
  2. extractionthe mixture was extracted with EtOAc
  3. washThe organic phase was washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give the crude product, which
  8. customwas purified by preparative TLC

Sources & evidence

ORD record
ord-a046225324904d0486c810ad810fd7cd
Source dataset
uspto-grants-2014_06
Patent number
US08748444B2

Reaction notes

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