(s)-Tert-butyl 2-(azidomethyl)morpholine-4-carboxylate → (R)-2-Aminomethyl-4-Boc-morpholine

HRID 1478556Notes

Reaction equation

HRID 1478556 reaction equation
[N:1]([CH2:4][C@H:5]1[O:10][CH2:9][CH2:8][N:7]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:6]1)=[N+]=[N-]>CO.[Pd]>[NH2:1][CH2:4][C@H:5]1[O:10][CH2:9][CH2:8][N:7]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:6]1

Participants

4

Reactant 1

HCID 90413392(s)-Tert-butyl 2-(azidomethyl)morpholine-4-carboxylate

Product 1

HCID 1515269(R)-2-Aminomethyl-4-Boc-morpholine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

(S)-tert-butyl 2-(azidomethyl)morpholine-4-carboxylate (31 g, 127.95 mmol) was dissolved in MeOH (400 ml), and Pd/C (5%, 6 g) was added, followed by stirring under H2 (gas) for 1 hour. After the completion of the reaction, the reaction mixture was filtered through celite, followed by drying, and then the next reaction was advanced.

Workup

  1. customAfter the completion of the reaction
  2. filtrationthe reaction mixture was filtered through celite
  3. customby drying
  4. customthe next reaction

Sources & evidence

ORD record
ord-6f2d2849e79b4c58bef264b858fd4f62
Source dataset
uspto-grants-2016_08
Patent number
US09403831B2

Reaction notes

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