Water → HCID 24967275, compound

HRID 1666440Notes

Reaction equation

HRID 1666440 reaction equation
C(OP(CC1C=CC=C(O[C:17]2[CH:22]=[CH:21][C:20](C(F)(F)F)=[CH:19][N:18]=2)C=1)(=O)OCC)C.[CH2:27]([O:29][C:30]1[CH:31]=[C:32]([CH:47]=[C:48]([O:50][C:51]2[CH:56]=[CH:55][C:54]([C:57]([F:60])([F:59])[F:58])=[CH:53][N:52]=2)[CH:49]=1)[CH:33]=[C:34]1[CH2:39][CH2:38][N:37]([C:40]([O:42]C(C)(C)C)=O)[CH2:36][CH2:35]1)[CH3:28].[H-].[Na+].C(OC([N:70]1CCC(=O)CC1)=O)(C)(C)C.O>C1COCC1.O1CCOCCOCCOCCOCC1>[CH2:27]([O:29][C:30]1[CH:31]=[C:32]([CH:47]=[C:48]([O:50][C:51]2[CH:56]=[CH:55][C:54]([C:57]([F:59])([F:58])[F:60])=[CH:53][N:52]=2)[CH:49]=1)[CH:33]=[C:34]1[CH2:35][CH2:36][N:37]([C:40]([NH:70][C:20]2[CH:19]=[N:18][CH:17]=[CH:22][CH:21]=2)=[O:42])[CH2:38][CH2:39]1)[CH3:28]

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 86623906HCID 86623906, compound

Product 1

HCID 24967275HCID 24967275, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 3633615-Crown-5CatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

tert-Butyl 4-(3-ethoxy-5-(5-(trifluoromethyl)pyridin-2-yloxy)benzylidene)piperidine-1-carboxylate [3-(5-Trifluoromethyl-pyridin-2-yloxy)-benzyl]-phosphonic acid diethyl ester (395 mg, 0.911 mmol) from Step 4 and 1,4,7,10,13-pentaoxacyclopentadecane (15-Crown-5, 0.003 mL, 0.0182 mmol) were combined in THF (3 mL). Sodium hydride (40 mg, 60% dispersion in mineral oil, 1.0 mmol) was added and the mixture was stirred for 30 min. A solution of 4-oxo-piperidine-1-carboxylic acid tert-butyl ester (200 mg, 1.0 mmol) in THF (2 mL) was added and the reaction was stirred at room temperature. After 16 h, water was added and the layers were separated. The aqueous layer was extracted with EtOAc and the combined organic layer was dried over anhydrous sodium sulfate, filtered and concentrated to afford the title compound as a thick oil (436 mg).

Workup

  1. stirringthe reaction was stirred at room temperature
  2. waitAfter 16 h
  3. customthe layers were separated
  4. extractionThe aqueous layer was extracted with EtOAc
  5. dry with materialthe combined organic layer was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-4cae50d1f73e4e0393abd1b4965066f6
Source dataset
uspto-grants-2011_10
Patent number
US08044052B2

Reaction notes

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