Hydrochloric Acid → tert-Butyl 3-(hydroxymethyl)azetidine-1-carboxylate

HRID 1910396Notes

Reaction equation

HRID 1910396 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([C:12](O)=[O:13])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CSC.B.Cl>C1COCC1>[OH:13][CH2:12][CH:10]1[CH2:11][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:9]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 27559811-Boc-Azetidine-3-carboxylic acidHCID 12423031(Dimethyl sulfide)trihydroboron

Product 1

HCID 10583745tert-Butyl 3-(hydroxymethyl)azetidine-1-carboxylateYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(tert-butoxycarbonyl)azetidine-3-carboxylic acid (2.0 g) in THF (30 ml) was added borane-dimethyl sulfide complex (4.0 ml; 10.0 M as borane) under ice-cooled bath, and the mixture was stirred for 8 hours at room temperature. 1 N HCl (10 ml) was added dropwise to the mixture under ice-cooled bath, and THF was removed under reduced pressure. The whole residue was extracted with EtOAc, and the extract was washed with brine and dried over MgSO4. Concentration under reduced pressure gave tert-butyl 3-(hydroxymethyl)azetidine-1-carboxylate (1.6 g).

Workup

  1. temperaturecooled bath
  2. temperaturecooled bath
  3. customTHF was removed under reduced pressure
  4. extractionThe whole residue was extracted with EtOAc
  5. washthe extract was washed with brine
  6. dry with materialdried over MgSO4
  7. concentrationConcentration under reduced pressure

Sources & evidence

ORD record
ord-ede4589585014cdcb27aefd2cb065c26
Source dataset
uspto-grants-2013_12
Patent number
US08603975B2

Reaction notes

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