4-(tert-Butoxycarbonyl)morpholine-3-carboxylic acid → Tert-butyl 3-(hydroxymethyl)morpholine-4-carboxylate

HRID 1479061Notes

Reaction equation

HRID 1479061 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH:9]1[C:14](O)=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2]>C1COCC1.CC(=O)OCC>[OH:15][CH2:14][CH:9]1[CH2:10][O:11][CH2:12][CH2:13][N:8]1[C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7]

Participants

4

Reactant 1

HCID 27601334-(tert-Butoxycarbonyl)morpholine-3-carboxylic acid

Product 1

HCID 5058359Tert-butyl 3-(hydroxymethyl)morpholine-4-carboxylateYield 64%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A 1M solution of borane-tetrahydrofuran complex in THF (8.65 mL; 8.65 mmol; 2 eq.) was added to a cold (0° C.) solution of morpholine-3,4-dicarboxylic acid 4-tert-butyl ester (1 g; 4.32 mmol; 1 eq.) in THF (10 mL) and the resulting mixture was stirred at room temperature for 1 hour. The solution was diluted with EA, washed with sat. aq. NaHCO3 then brine, dried over magnesium sulfate and concentrated in vacuo. Purification by column chromatography (EA/heptane) afforded the title compound (600 mg, 64%) as a colourless oil.

Workup

  1. washwashed with sat. aq. NaHCO3
  2. dry with materialbrine, dried over magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customPurification by column chromatography (EA/heptane)

Sources & evidence

ORD record
ord-99429a5812e74cf8bfb846c6f71eea96
Source dataset
uspto-grants-2016_08
Patent number
US09403835B2

Reaction notes

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