Sodium Hydroxide → 3-Hydroxymethyl-azetidine-1-carboxylic acid benzyl ester

HRID 887657Notes

Reaction equation

HRID 887657 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:14][CH:13]([C:15](O)=[O:16])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B.C1COCC1.[OH-].[Na+]>C1COCC1>[CH2:1]([O:8][C:9]([N:11]1[CH2:14][CH:13]([CH2:15][OH:16])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 2723981Borane;tetrahydrofuranHCID 109882141-[(Benzyloxy)carbonyl]azetidine-3-carboxylic acid

Product 1

HCID 448291173-Hydroxymethyl-azetidine-1-carboxylic acid benzyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of azetidine-1,3-dicarboxylic acid monobenzyl ester (6.4 g) in THF (200 mL) was added BH3.THF (6 eq, 163 mL, 1M solution) dropwise via an addition funnel at −40 C under an N2 atmosphere. The solution was warmed to RT and stirred overnight. To the reaction, 5N NaOH (50 mL) was added and then concentrated under vacuum. The resulting aqueous solution was extracted with Et2O (3×100 mL). The organic layer was dried over Na2SO4 and evaporated to give the title compound which was used without further purification.

Workup

  1. additionwas added
  2. concentrationconcentrated under vacuum
  3. extractionThe resulting aqueous solution was extracted with Et2O (3×100 mL)
  4. dry with materialThe organic layer was dried over Na2SO4
  5. customevaporated

Sources & evidence

ORD record
ord-802acf4bed344592907f856593ed0faf
Source dataset
uspto-grants-2012_08
Patent number
US08247430B2

Reaction notes

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