(R)-tert-Butyl 2-((benzyloxy)methyl)morpholine-4-carboxylate → (R)-N-Boc-2-hydroxymethylmorpholine

HRID 451726Notes

Reaction equation

HRID 451726 reaction equation
C([O:8][CH2:9][C@@H:10]1[O:15][CH2:14][CH2:13][N:12]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:11]1)C1C=CC=CC=1>CCO.[Pd]>[OH:8][CH2:9][C@@H:10]1[O:15][CH2:14][CH2:13][N:12]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:11]1

Participants

4

Reactant 1

HCID 53989854(R)-tert-Butyl 2-((benzyloxy)methyl)morpholine-4-carboxylate

Product 1

HCID 1512576(R)-N-Boc-2-hydroxymethylmorpholineYield 99.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of (R)-tert-butyl 2-(benzyloxymethyl)morpholine-4-carboxylate (8.33 g, 27.1 mmol) in EtOH was added Pd—C (wet, 3.6 g), and the resulting mixture was stirred at rt under a H2 balloon overnight. After filtration, the solvent was removed under vacuum, and the residue was purified by flash column chromatography to give (R)-tert-butyl 2-(hydroxymethyl)morpholine-4-carboxylate (5.84 g, 99%) as a clear oil. 1H NMR (400 MHz, CDCl3): 3.88 (d, 2H), 3.82 (br, 1H), 3.64 (d, 1H), 3.56 (m, 3H), 2.94 (m, 1H), 2.76 (m, 1H), 1.90 (br, 1H), 1.44 (s, 9H); MS m/z 218 (M+H+).

Workup

  1. filtrationAfter filtration
  2. customthe solvent was removed under vacuum
  3. customthe residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-5788c0782880405a94e439e477743645
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Reaction notes

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