Hydrochloric Acid → 4-Aminotetrahydropyran-4-carboxylic acid benzyl ester

HRID 1596025Notes

Reaction equation

HRID 1596025 reaction equation
[CH2:1]([O:8][C:9]([C:11]1([N:17]=C(C2C=CC=CC=2)C2C=CC=CC=2)[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>C(OCC)C>[CH2:1]([O:8][C:9]([C:11]1([NH2:17])[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 537582684-[N-(diphenylmethylene)amino]tetrahydropyran-4-carboxylic acid benzyl ester

Product 1

HCID 539944184-Aminotetrahydropyran-4-carboxylic acid benzyl ester

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 4-[N-(diphenylmethylene)amino]tetrahydropyran-4-carboxylic acid benzyl ester (16.0 grams, 0.047 mole) in diethyl ether (120 mL) is added 1M aqueous hydrochloric acid solution (100 mL). The mixture is stirred vigorously at room temperature for 16 hours. The layers are separated and the aqueous layer washed with diethyl ether. The aqueous layer is brought to pH 10 with dilute aqueous ammonium hydroxide solution and extracted with dichloromethane. The organic extract is dried over sodium sulfate and concentrated to give 4-aminotetrahydropyran-4-carboxylic acid benzyl ester.

Workup

  1. customThe layers are separated
  2. washthe aqueous layer washed with diethyl ether
  3. extractionextracted with dichloromethane
  4. extractionThe organic extract
  5. dry with materialis dried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-afa153954802420695d8f646e531dc12
Source dataset
uspto-grants-2001_09
Patent number
US06288246B1

Reaction notes

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