Hydrochloric Acid → 1-(1,1-Dimethylethyl) 3,6-dihydro-1,3(2H)-pyridinedicarboxylate

HRID 1003383Notes

Reaction equation

HRID 1003383 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]=[C:10]([C:14]([OH:16])=[O:15])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([Li])CCC.CCCCCC.C(NC(C)C)(C)C.Cl>O1CCCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[CH:11][CH:10]([C:14]([OH:16])=[O:15])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 7912DiisopropylamineHCID 8058HexaneHCID 130325691-Boc-1,2,5,6-tetrahydropyridine-3-carboxylic acidHCID 178418339Butyllithium

Product 1

HCID 113791591-(1,1-Dimethylethyl) 3,6-dihydro-1,3(2H)-pyridinedicarboxylateYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1-tert-butoxycarbonyl-1,2,5,6-tetrahydropyridine-3-carboxylic acid (6.5 g, 28.6 mmol) in dry tetrahydrofuran (150 ml) was added dropwise to a mixture of 2.5 M butyllithium in hexane (25 ml, 62.5 mmol) and diisopropylamine (6.37 g, 63.1 mmol) in dry tetrahydrofuran (150 ml) at <-65° C. Stirring was continued for 20 min. -10°C. The mixture was poured into 1 M aqueous HCl (100 ml) while cooling with ice. The resulting mixture was extracted several times with ethyl acetate (a total of 500 ml). The organic layer was dried over magnesium sulphate and evaporated to dryness in vacuo to give 1-tert-butoxycarbonyl-1,2,3,6-tetrahydropyridine-3-carboxylic acid (Yield: 6.3 g, 97%).

Workup

  1. temperaturewhile cooling with ice
  2. extractionThe resulting mixture was extracted several times with ethyl acetate (a total of 500 ml)
  3. dry with materialThe organic layer was dried over magnesium sulphate
  4. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-756a4d3762a345c4918d7902bb7f4c43
Source dataset
uspto-grants-2000_04
Patent number
US06046214

Reaction notes

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