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

HRID 1712649Notes

Reaction equation

HRID 1712649 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 aluminium hydride (128 mg) was placed in a round bottomed flask, and suspended in tetrahydrofuran (30 ml). The suspension was cooled in an ice bath, and a solution of methyl 1-tert-butoxycarbonylazetidine-3-carboxylate (970 mg) in tetrahydrofuran (10 ml) was added gradually, followed by stirring at the same temperature under a nitrogen atmosphere for 1 hour. Water (0.13 ml), a 5N aqueous solution of sodium hydroxide (0.13 ml) and water (0.39 ml) was added to the reaction mixture with cooling in an ice bath, followed by stirring at the same temperature for 1 hour. Insoluble matter in the reaction mixture was removed by filtration. The filtrate was concentrated to give the title compound (805 mg, 95.3%) as a colorless oil.

Workup

  1. temperatureThe suspension was cooled in an ice bath
  2. temperaturewith cooling in an ice bath
  3. stirringby stirring at the same temperature for 1 hour
  4. customInsoluble matter in the reaction mixture was removed by filtration
  5. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-54b5aa80f3374815a51e11013d9e45a9
Source dataset
uspto-grants-2010_09
Patent number
US07790885B2

Reaction notes

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