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

HRID 887344ノート

反応式

HRID 887344 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-95080666486a4f23a9f354eea91e27a6
出典データセット
uspto-grants-2012_08
特許番号
US08247421B2

反応ノート

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