Hydrochloric Acid → HCID 66731619, compound

HRID 1963239Notes

Reaction equation

HRID 1963239 reaction equation
[CH3:1][N:2]1[N:6]=[N:5][C:4]([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: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:4]1[N:5]=[N:6][N:2]([CH3:1])[N:3]=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 86646601HCID 86646601, compound

Product 1

HCID 66731619HCID 66731619, compoundYield 101.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

1-Benzyl 4-ethyl 2-(2-methyl-2H-tetrazol-5-yl)piperidine-1,4-dicarboxylate (0.92 g, 2.36 mmol) was dissolved in THF (10 mL) and water (10 mL) and LiOH (0.239 g, 9.98 mmol) was added. The mixture was stirred at room temperature for 1 h 10 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-(2-methyl-2H-tetrazol-5-yl)piperidine-4-carboxylic acid (828 mg, quant.). 1H NMR (400 MHz, cdcl3) δ 1.80-1.91 (m, 1H), 2.01-2.11 (m, 1H), 2.34 (dt, 1H), 2.63-2.79 (m, 2H), 3.55-3.65 (m, 1H), 4.01-4.09 (m, 1H), 4.24 (s, 3H), 5.13 (d, 2H), 5.60 (dd, 1H), 7.27-7.39 (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-8c562489419546e588a0c32deb1e5d55
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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