Hydrochloric Acid → HCID 86607415, compound

HRID 733103Notes

Reaction equation

HRID 733103 reaction equation
[CH2:1]([N:8]1[N:12]=[N:11][C:10]([CH:13]([CH:19]2[CH2:23][CH2:22][CH2:21][CH2:20]2)[C:14](OCC)=[O:15])=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].C([Al+]CC(C)C)C(C)C.Cl.[NH4+].[Cl-]>C(Cl)Cl>[CH2:1]([N:8]1[N:12]=[N:11][C:10]([CH:13]([CH:19]2[CH2:23][CH2:22][CH2:21][CH2:20]2)[CH:14]=[O:15])=[N:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 21225700DiisobutylaluminumhydrideHCID 86607414HCID 86607414, compound

Product 1

HCID 86607415HCID 86607415, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

To a stirred mixture of 2-benzyl-α-cyclopentyl-2H-tetrazole-5-acetic acid, ethyl ester (2.92 g, 9.72 mmol, step 2 of Example 14) in CH2Cl2 (50 mL) at −78° C. was added diisobutylaluminium hydride (1.0 M in toluene, 22.5 mL, 22.5 mmol). The resulting mixture was stirred at −78° C. for 5 h. To the mixture were added 2 M aqueous HCl (50 mL) and saturated aqueous NH4Cl (10 mL). The organic layer was separated, dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue was chromatographed on a column of silica gel eluting with Hexane/ethyl acetate (10:1) to give 862 mg (35%) of the title compound.

Workup

  1. customThe organic layer was separated
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was chromatographed on a column of silica gel eluting with Hexane/ethyl acetate (10:1)

Sources & evidence

ORD record
ord-088c3696b75d40b58ab955c6431b5ba4
Source dataset
uspto-grants-2009_09
Patent number
US07589109B2

Reaction notes

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