Ammonia → benzyl 4-[3-(2-hydroxyethyl)-2-oxotetrahydropyrimidin-1(2H)-yl]piperidin-1-carboxylate

HRID 20236Notes

Reaction equation

HRID 20236 reaction equation
C([O:5][C:6]([CH2:8][N:9]1[CH2:14][CH2:13][CH2:12][N:11]([CH:15]2[CH2:20][CH2:19][N:18]([C:21]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[O:22])[CH2:17][CH2:16]2)[C:10]1=[O:31])=O)(C)(C)C.[BH4-].[Li+].N>C1COCC1>[OH:5][CH2:6][CH2:8][N:9]1[CH2:14][CH2:13][CH2:12][N:11]([CH:15]2[CH2:20][CH2:19][N:18]([C:21]([O:23][CH2:24][C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)=[O:22])[CH2:17][CH2:16]2)[C:10]1=[O:31]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 4148881Lithium borohydrideHCID 68417510benzyl 4-[3-(tert-butoxycarbonylmethyl)-2-oxotetrahydropyrimidin-1(2H)-yl]piperidin-1-carboxylate

Product 1

HCID 68420920benzyl 4-[3-(2-hydroxyethyl)-2-oxotetrahydropyrimidin-1(2H)-yl]piperidin-1-carboxylateYield 99.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of benzyl 4-[3-(tert-butoxycarbonylmethyl)-2-oxotetrahydropyrimidin-1(2H)-yl]piperidin-1-carboxylate (0.60 g) obtained in Example 35a) and lithium borohydride (0.091 g) in THF (15 mL) was refluxed for 5 hours. The reaction mixture was allowed to stand at room temperature and poured into an aqueous saturated ammonia solution under ice-cooling. The organic layer was separated, and the aqueous layer was extracted with dichloromethane. The organic layers were combined, washed with a saturated saline solution, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate to ethyl acetate/methanol=95/5) to obtain the title compound (0.50 g, 99%) as a colorless oil.

Workup

  1. customto stand at room temperature
  2. temperaturecooling
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with dichloromethane
  5. washwashed with a saturated saline solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (ethyl acetate to ethyl acetate/methanol=95/5)

Sources & evidence

ORD record
ord-22cf86de9b794a88b31dc6c8e579605e
Source dataset
uspto-grants-2010_06
Patent number
US07745623B2

Reaction notes

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