Borane → tert-Butyl (2S)-2-(hydroxymethyl)morpholine-4-carboxylate

HRID 530459Notes

Reaction equation

HRID 530459 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][O:11][C@H:10]([C:14](O)=[O:15])[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].B>C1COCC1>[OH:15][CH2:14][C@H:10]1[O:11][CH2:12][CH2:13][N:8]([C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[CH2:9]1

Participants

4

Reactant 2

HCID 6331BoraneHCID 1519383(2S)-4-[(tert-butoxy)carbonyl]morpholine-2-carboxylic acid

Product 1

HCID 1512577tert-Butyl (2S)-2-(hydroxymethyl)morpholine-4-carboxylateYield 92.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(S)—N-Boc-2-morpholine carboxylic acid (2.00 g, 8.65 mmol) was dissolved in THF (30 mL) and borane (25.9 mL, 1.0 M in THF, 25.9 mmol) was added dropwise. The reaction mixture was heated at reflux for 2.5 h and quenched with water (10 mL). The reaction mixture was concentrated in vacuo and the residue dissolved in DCM (30 mL), washed with sat aq Na2CO3 (2×20 mL), dried (MgSO4) and concentrated in vacuo to give the crude title compound (1.74 g, 92%) as a pale yellow oil. LCMS (ES+): 240.3 [MNa]+.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 2.5 h
  3. customquenched with water (10 mL)
  4. concentrationThe reaction mixture was concentrated in vacuo
  5. dissolutionthe residue dissolved in DCM (30 mL)
  6. washwashed with sat aq Na2CO3 (2×20 mL)
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2d17908cc3bf47d881ea79efafbc96e9
Source dataset
uspto-grants-2016_05
Patent number
US09353086B2

Reaction notes

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