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

HRID 887344

반응식

HRID 887344 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-95080666486a4f23a9f354eea91e27a6
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08247421B2

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