Water → tert-Butyl 3-(hydroxymethyl)azetidine-1-carboxylate

HRID 2265702Notes

Reaction equation

HRID 2265702 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([O:11][C:12]([N:14]1[CH2:17][CH:16]([C:18](OC)=[O:19])[CH2:15]1)=[O:13])([CH3:10])([CH3:9])[CH3:8].O.[OH-].[Na+]>O1CCCC1>[OH:19][CH2:18][CH:16]1[CH2:17][N:14]([C:12]([O:11][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:13])[CH2:15]1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 446076271-tert-Butyl 3-methyl azetidine-1,3-dicarboxylate

Product 1

HCID 10583745tert-Butyl 3-(hydroxymethyl)azetidine-1-carboxylateYield 95.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Lithium aluminum hydride (128 mg) was placed in a round-bottomed flask and suspended in tetrahydrofuran (30 ml). This was cooled in an ice bath, and a solution of methyl 1-tert-butoxycarbonylazetidine-3-carboxylate (970 mg) in tetrahydrofuran (10 ml) was gradually added thereto, followed by stirring under a nitrogen atmosphere at the same temperature for 1 hr. To the reaction mixture were added water (0.13 ml) and a 5N aqueous solution of sodium hydroxide (0.13 ml) and water (0.39 ml) while cooling in an ice bath, followed by stirring at the same temperature for 1 hr. Insoluble matter in the reaction mixture was removed by filtration. The filtrate was concentrated to provide the titled compound as a colorless oil (805 mg, 95.3%).

Workup

  1. temperatureThis was cooled in an ice bath
  2. stirringby stirring at the same temperature for 1 hr
  3. customInsoluble matter in the reaction mixture was removed by filtration
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-4e4e309801a444929b2f5fcc31ad1a67
Source dataset
uspto-grants-2010_12
Patent number
US07855290B2

Reaction notes

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