Hydrochloric Acid → HCID 66734697, compound

HRID 1963240Notes

Reaction equation

HRID 1963240 reaction equation
[CH3:1][N:2]1[C:6]([CH:7]2[CH2:12][CH:11]([C:13]([O:15]CC)=[O:14])[CH2:10][CH2:9][N:8]2[C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:19])=[N:5][N:4]=[N:3]1.[Li+].[OH-].Cl>C1COCC1.O>[CH2:21]([O:20][C:18]([N:8]1[CH2:9][CH2:10][CH:11]([C:13]([OH:15])=[O:14])[CH2:12][CH:7]1[C:6]1[N:2]([CH3:1])[N:3]=[N:4][N:5]=1)=[O:19])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 66734713HCID 66734713, compound2×

Product 1

HCID 66734697HCID 66734697, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

1-Benzyl 4-ethyl 2-(1-methyl-1H-tetrazol-5-yl)piperidine-1,4-dicarboxylate (1.14 g, 2.93 mmol) (from reference compound 36, step 6) was dissolved in THF (10 mL) and water (10 mL) and LiOH (0.280 g, 11.69 mmol) was added. The mixture was stirred at room temperature for 30 min and then diluted with water and acidified with 2 M HCl. The aqueous phase was extracted 3 times with EtOAc, the combined organic phase dried over Na2SO4 and evaporated to yield 1-(Benzyloxycarbonyl)-2-(1-methyl-1H-tetrazol-5-yl)piperidine-4-carboxylic acid (990 mg, 98%). 1H NMR (400 MHz, cdcl3) δ 1.89-2.01 (m, 1H), 2.15-2.24 (m, 1H), 2.27-2.36 (m, 1H), 2.50-2.61 (m, 1H), 2.78 (p, 1H), 3.68-3.80 (m, 1H), 3.91-4.09 (m, 4H), 5.08 (q, 2H), 5.44 (t, 1H), 7.23-7.39 (m, 5H). MS m/z 346 (M+H)+

Workup

  1. extractionThe aqueous phase was extracted 3 times with EtOAc
  2. dry with materialthe combined organic phase dried over Na2SO4
  3. customevaporated

Sources & evidence

ORD record
ord-2488aa50466b41d0ab374b9484a1a6df
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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