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Tetrahydro-4H-pyran-4-one → HCID 69122283, compound

HRID 2064094
Notes
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Reaction equation

HRID 2064094 reaction equation
[ClH:1].[F:2][CH:3]([F:21])[O:4][C:5]1[CH:6]=[CH:7][C:8]2[NH:12][C:11](=[O:13])[N:10]([CH:14]3[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]3)[C:9]=2[CH:20]=1.[O:22]1[CH2:27][CH2:26][C:25](=O)[CH2:24][CH2:23]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>C(N(CC)CC)C.ClCCCl>[ClH:1].[F:21][CH:3]([F:2])[O:4][C:5]1[CH:6]=[CH:7][C:8]2[NH:12][C:11](=[O:13])[N:10]([CH:14]3[CH2:15][CH2:16][N:17]([CH:25]4[CH2:26][CH2:27][O:22][CH2:23][CH2:24]4)[CH2:18][CH2:19]3)[C:9]=2[CH:20]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 121599Tetrahydro-4H-pyran-4-oneHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 57423922HCID 57423922, compound

Product 1

HCID 69122283HCID 69122283, compoundYield 68.6%

Reagents, catalysts & solvents 2

HCID 11
1,2-Dichloroethane
Solvent
HCID 8471TriethylamineSolvent

Procedure

6-[(Difluoromethyl)oxy]-1-(4-piperidinyl)-1,3-dihydro-2H-benzimidazol-2-one hydrochloride (D54, 0.3 g) 1,2-dichloroethane (10 ml) and triethylamine (0.5 ml), tetrahydro-4H-pyran-4-one (0.6 g), sodium triacetoxyborohydride (0.6 g) was stirred at room temperature over 3 days. The mixture was poured into sodium bicarbonate solution and extracted with dichloromethane. The organic phase was separated, washed with brine and the solvent was removed and the residue was chromatographed on silica gel eluted with dichloromethane/2M ammonia in methanol 0-10%. The resulting product was dissolved in a mixture of methanol and dichloromethane, treated with 1M hydrogen chloride in ether and the solvent was removed. Recrystallisation from methanol gave the title compound as a white solid (0.26 g). Mass Spectrum 368 M+H+

Workup

  1. extractionextracted with dichloromethane
  2. customThe organic phase was separated
  3. washwashed with brine
  4. customthe solvent was removed
  5. customthe residue was chromatographed on silica gel
  6. washeluted with dichloromethane/2M ammonia in methanol 0-10%
  7. dissolutionThe resulting product was dissolved in a mixture of methanol and dichloromethane
  8. additiontreated with 1M hydrogen chloride in ether
  9. customthe solvent was removed
  10. customRecrystallisation from methanol

Sources & evidence

ORD record
ord-5b0e0ffdbf4e4ba996af0acf0883fa53
Source dataset
uspto-grants-2012_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08288413B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes