Sodium Hydroxide → tert-Butyl 2-(hydroxymethyl)morpholine-4-carboxylate

HRID 1864002Notes

Reaction equation

HRID 1864002 reaction equation
C1(C([O:9][CH2:10][CH:11]2[O:16][CH2:15][CH2:14][N:13]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:12]2)=O)C=CC=CC=1.[OH-].[Na+]>CO>[OH:9][CH2:10][CH:11]1[O:16][CH2:15][CH2:14][N:13]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:12]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 686616651,1-Dimethylethyl 2-{[(phenylcarbonyl)oxy]methyl}-4-morpholinecarboxylate

Product 1

HCID 5201202tert-Butyl 2-(hydroxymethyl)morpholine-4-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1,1-dimethylethyl 2-{[(phenylcarbonyl)oxy]methyl}-4-morpholinecarboxylate (enantiomer E2) (1.08 g, 3.36 mmol) in methanol (30 mL) with 6N NaOH (5.6 mL. 33.6 mmol) was stirred at room temperature for 2 h. The methanol was removed under reduced pressure and the resulting mixture was partitioned between ethyl acetate and water. The organic extract was washed with brine, dried over sodium sulfate and solvent removed under reduced pressure to give the desired compound. 1H NMR (400 MHz, DMSO-d6) d ppm 1.41 (s, 50H) 3.25-3.37 (m, 22H) 3.39-3.46 (m, 7H) 3.70 (d, J=12.88 Hz, 6H) 3.76-3.88 (m, 10H) 4.78 (t, J=5.68 Hz, 5H)

Workup

  1. customThe methanol was removed under reduced pressure
  2. customthe resulting mixture was partitioned between ethyl acetate and water
  3. extractionThe organic extract
  4. washwas washed with brine
  5. dry with materialdried over sodium sulfate and solvent
  6. customremoved under reduced pressure

Sources & evidence

ORD record
ord-f99bcd423bde489f84909496e70d442f
Source dataset
uspto-grants-2009_12
Patent number
US07625890B2

Reaction notes

Loading…