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Triethylamine → tert-Butyl 4-[2-(tetrahydro-2H-pyran-4-yl)-1,3-oxazol-4-yl]piperidine-1-carboxylate

HRID 716712
Notes
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Reaction equation

HRID 716712 reaction equation
Br[CH2:2][C:3]([CH:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]1)=O.[O:18]1[CH2:23][CH2:22][CH:21]([C:24]([NH2:26])=[O:25])[CH2:20][CH2:19]1.CCN(CC)CC.CC(OC(OC(OC(C)(C)C)=O)=O)(C)C>CN1C(=O)N(C)CCC1.O.ClCCl>[O:18]1[CH2:23][CH2:22][CH:21]([C:24]2[O:25][CH:2]=[C:3]([CH:5]3[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]3)[N:26]=2)[CH2:20][CH2:19]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 90495Di-tert-butyl dicarbonateHCID 13197203Oxane-4-carboxamideHCID 18187487tert-Butyl 4-(2-Bromoacetyl)piperidine-1-carboxylate

Product 1

HCID 70171103tert-Butyl 4-[2-(tetrahydro-2H-pyran-4-yl)-1,3-oxazol-4-yl]piperidine-1-carboxylate

Reagents, catalysts & solvents 3

HCID 962
Water
Solvent
HCID 6344DichloromethaneSolvent
HCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-Solvent

Procedure

tert-Butyl 4-(bromoacetyl)piperidine-1-carboxylate (1.07 g, 3.49 mmol) and tetrahydro-2H-pyran-4-carboxamide (0.95 g, 7.36 mmol) were mixed heated in DMPU (6.99 mL) at 150° C. for 4 hrs. LC-MS indicated that the reaction was completed and the product showed loss of Boc group. Et3N (1.46 mL, 10.5 mol) and Boc2O (0.915 g, 4.19 mmol) were added and the mixture was stirred at RT for 30 min. The reaction was diluted with water and dichloromethane. The two layers were separated and the organic layer was extracted with dichloromethane. The combined organic layers were washed with H2O (twice) and brine, dried over Na2SO4, filtered and conc. The crude (still containing DMPU) was used without purification. LC-MS: [M+H]+=337.4.

Workup

  1. customThe two layers were separated
  2. extractionthe organic layer was extracted with dichloromethane
  3. washThe combined organic layers were washed with H2O (twice) and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customconc. The crude (still containing DMPU) was used without purification

Sources & evidence

ORD record
ord-59ee269021374425940789826f7f61ca
Source dataset
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09193697B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes