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

HRID 1853468Notes

Reaction equation

HRID 1853468 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-bf3b9d38dac4408fbf540a9a4074077e
Source dataset
uspto-grants-2015_02
Patent number
US08962642B2

Reaction notes

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