Methanol → tert-Butyl 2-(hydroxymethyl)morpholine-4-carboxylate

HRID 1249708Notes

Reaction equation

HRID 1249708 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][O:11][CH:10]([C:14](O)=[O:15])[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].B#B.CO>C1COCC1>[C:1]([N:8]1[CH2:13][CH2:12][O:11][CH:10]([CH2:14][OH:15])[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 27559654-((Tert-butoxy)carbonyl)morpholine-2-carboxylic acidHCID 6328200Diboron

Product 1

HCID 5201202tert-Butyl 2-(hydroxymethyl)morpholine-4-carboxylateYield 128.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a cooled (0° C.) solution of Boc-2-carboxymorpholine (1.01 g, 4.3 mmol) in anhydrous THF under argon (25 mL) was added 10.8 mL of a 1M solution of diborane in THF. After stirring at room temperature overnight, methanol was added (10 mL) and the reaction was heated to reflux for 30 min. The solvent was evaporated and the residue was dissolved in ethyl acetate, washed with brine. The combined organic layers were dried (MgSO4) and the solvent was evaporated to yield a colorless liquid (1.2 g) that was used in the next step without further purification.

Workup

  1. temperaturethe reaction was heated
  2. temperatureto reflux for 30 min
  3. customThe solvent was evaporated
  4. dissolutionthe residue was dissolved in ethyl acetate
  5. washwashed with brine
  6. dry with materialThe combined organic layers were dried (MgSO4)
  7. customthe solvent was evaporated

Sources & evidence

ORD record
ord-850e5bba48b94ebfab87f9596c220ebe
Source dataset
uspto-grants-2002_01
Patent number
US06335338B1

Reaction notes

Loading…