(-)-Mandelic acid → tert-butyl 4-((1R)-1-aminoethyl)piperidine-1-carboxylate

HRID 887344Notes

Reaction equation

HRID 887344 reaction equation
[NH2:1][CH:2]([CH:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1)[CH3:3].C(O)(=O)[C@@H](C1C=CC=CC=1)O>CC(C)=O>[NH2:1][C@@H:2]([CH:4]1[CH2:5][CH2:6][N:7]([C:10]([O:12][C:13]([CH3:14])([CH3:16])[CH3:15])=[O:11])[CH2:8][CH2:9]1)[CH3:3]

Participants

4

Reactant 2

HCID 11914(-)-Mandelic acidHCID 22647295tert-Butyl 4-(1-aminoethyl)piperidine-1-carboxylate

Product 1

HCID 59414623tert-butyl 4-((1R)-1-aminoethyl)piperidine-1-carboxylateYield 19%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

From the mother liquor of the above mentioned first crystallization tert-butyl 4-(1-aminoethyl)piperidine-1-carboxylate (20 g, 88 mmol) could be isolated (enriched in the other enantiomer). To the material was added (R)-(−)-mandelic acid (14 g, 92 mmol) and acetone (300 mL). The mixture was heated until a clear solution was obtained and allowed to cool to room temperature while stirring. The obtained precipitate was collected, rinsed with some acetone and recrystallized once as described above. After acid base separation, (R)-tert-butyl 4-(1-aminoethyl)piperidine-1-carboxylate was obtained (7.5 g, 99+% ee, 19% yield).

Workup

  1. customcould be isolated (
  2. temperatureThe mixture was heated until a clear solution
  3. customwas obtained
  4. customThe obtained precipitate was collected
  5. washrinsed with some acetone
  6. customrecrystallized once
  7. customAfter acid base separation

Sources & evidence

ORD record
ord-95080666486a4f23a9f354eea91e27a6
Source dataset
uspto-grants-2012_08
Patent number
US08247421B2

Reaction notes

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