Acetic Acid → cis-3-Butoxycarbonylamino-2-hydroxymethyl-4-oxoazetidine

HRID 1862880Notes

Reaction equation

HRID 1862880 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]1[C:12](=[O:13])[NH:11][CH:10]1[C:14]([O:16]C)=O)=[O:7])([CH3:4])(C)C.[BH4-].[Na+].[C:20](O)(=O)[CH3:21].[BH4-]>O1CCCC1.O>[CH2:1]([O:5][C:6]([NH:8][C@H:9]1[C:12](=[O:13])[NH:11][C@H:10]1[CH2:14][OH:16])=[O:7])[CH2:4][CH2:20][CH3:21]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 28123BorohydrideHCID 4311764Sodium borohydrideHCID 12762152Methyl 3-t-butoxycarbonylamino-4-oxoazetidine-2-carboxylate

Product 1

HCID 70600216cis-3-Butoxycarbonylamino-2-hydroxymethyl-4-oxoazetidineYield 50%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2.0 g (8.2 mmole) of methyl 3-t-butoxycarbonylamino-4-oxoazetidine-2-carboxylate in 20 ml of tetrahydrofuran is cooled in ice and a solution of 0.75 g (20 mmole) of sodium borohydride in 10 ml of water is added. The mixture is stirred 20 min at 0° and then 1.5 hr at room temperature. Acetic acid is added dropwise to decompose the excess borohydride and the mixture is concentrated in vacuum. The residue is diluted with brine and extracted with ethyl acetate. The organic phase is washed with brine and 5% NaHCO3 ; dried over magnesium sulfate and evaporated to dryness to give 0.9 g (50%) of the title product as white crystals, mp 128°-131°.

Workup

  1. custom1.5 hr
  2. customat room temperature
  3. concentrationthe mixture is concentrated in vacuum
  4. additionThe residue is diluted with brine
  5. extractionextracted with ethyl acetate
  6. washThe organic phase is washed with brine and 5% NaHCO3
  7. dry with materialdried over magnesium sulfate
  8. customevaporated to dryness

Sources & evidence

ORD record
ord-dda24b07b266471c8b7c11eb59ba9e3f
Source dataset
uspto-grants-1979_09
Patent number
US04166816

Reaction notes

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