Sodium Hydroxide → 1-(Diphenylmethyl)azetidine-3-carboxylic acid

HRID 1029635Notes

Reaction equation

HRID 1029635 reaction equation
[C:1]1([CH:7]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:8]2[CH2:11][CH:10]([C:12]([O:14]C)=[O:13])[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>CO.O1CCCC1>[C:16]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[N:8]2[CH2:11][CH:10]([C:12]([OH:14])=[O:13])[CH2:9]2)[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 2759842Methyl 1-(diphenylmethyl)azetidine-3-carboxylate

Product 1

HCID 27354401-(Diphenylmethyl)azetidine-3-carboxylic acidYield 92.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(diphenylmethyl)-3-methoxycarbonylazetidine (28 g) in methanol (270 ml) and tetrahydrofuran (130 ml) was added 1N sodium hydroxide (115 ml) and the solution was stirred at room temperature for 1.5 hours. The solution was then concentrated to remove organic solvents under reduced pressure. The resultant aqueous solution was adjusted to pH 2.95 with 10% hydrochloric acid, and resulting precipitates were collected by filtration, washed with water and dried to give 1-(diphenylmethyl)-3-carboxyazetidine (24.7 g).

Workup

  1. concentrationThe solution was then concentrated
  2. customto remove organic solvents under reduced pressure
  3. customresulting
  4. customprecipitates
  5. filtrationwere collected by filtration
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-eb6769a95d484a969b52426dd2c14f2b
Source dataset
uspto-grants-1992_04
Patent number
US05102877

Reaction notes

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