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Water → Methyl 4-[(1-Boc-piperidin-4-ylidene)methyl]benzoate

HRID 635232
Notes
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Reaction equation

HRID 635232 reaction equation
[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10]P(OC)(OC)=O)=[CH:6][CH:5]=1.C([N-]C(C)C)(C)C.[Li+].[O:26]([C:31]([N:33]1[CH2:38][CH2:37][C:36](=O)[CH2:35][CH2:34]1)=[O:32])[C:27]([CH3:30])([CH3:29])[CH3:28].O>C1COCC1.C(OCC)(=O)C>[C:27]([O:26][C:31]([N:33]1[CH2:38][CH2:37][C:36](=[CH:10][C:7]2[CH:6]=[CH:5][C:4]([C:3]([O:2][CH3:1])=[O:17])=[CH:9][CH:8]=2)[CH2:35][CH2:34]1)=[O:32])([CH3:30])([CH3:28])[CH3:29]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 962WaterHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 2724682Lithium diisopropylamideHCID 108011704-(Dimethoxy-phosphorylmethyl)-benzoic acid methyl ester2×

Product 1

HCID 10616499Methyl 4-[(1-Boc-piperidin-4-ylidene)methyl]benzoateYield 35%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-78 °C

Procedure

The crude product (compound 48) was dissolved in dry THF (200 mL) under N2 and cooled to −78° C. Lithium diisopropylamide (32.7 mL 1.5 M in hexanes, 49 mmol) was added dropwise. The solution was allowed to warm to room temperature. A solution of compound 46 (9.76 g, 49 mmol in 100 mL dry THF) was added to the reaction dropwise and was stirred under N2 for 12 hrs. Water (300 mL) and ethyl acetate (300 mL) were added to the reaction mixture and extracted. The aqueous phase was washed with ethyl acetate (2×300 mL). The combined ethyl acetate was dried over MgSO4 and evaporated to give a crude product, which was purified by silica gel chromatography (0-33% ethyl acetate in hexanes) to provide compound 49 as a white solid (5.64 g, 35%).

Workup

  1. temperatureto warm to room temperature
  2. extractionextracted
  3. washThe aqueous phase was washed with ethyl acetate (2×300 mL)
  4. dry with materialThe combined ethyl acetate was dried over MgSO4
  5. customevaporated
  6. customto give a crude product, which
  7. customwas purified by silica gel chromatography (0-33% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-4e7d1400b1eb4207a9eb2947d00bd81a
Source dataset
uspto-grants-2001_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06187792B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes