Formic Acid → rac-methyl (1R,2R)-2-amino-1-hydroxycyclopentane-1-carboxylate

HRID 736808ノート

反応式

HRID 736808 の反応式
C([N:8]([C@@H](C1C=CC=CC=1)C)[C@@H:9]1[CH2:13][CH2:12][CH2:11][C@:10]1([OH:18])[C:14]([O:16][CH3:17])=[O:15])C1C=CC=CC=1.C(O)=O>CO.[Pd]>[NH2:8][C@@H:9]1[CH2:13][CH2:12][CH2:11][C@:10]1([OH:18])[C:14]([O:16][CH3:17])=[O:15]

参加物

5

反応物 2

HCID 284Formic AcidHCID 86607904methyl (1R,2R)-2-{benzyl[(1R)-1-phenylethyl]amino}-1-hydroxycyclopentanecarboxylate

生成物 1

HCID 86607905rac-methyl (1R,2R)-2-amino-1-hydroxycyclopentane-1-carboxylate収率 124.1%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 887Methanol溶媒

反応条件

温度
40 °C

実験手順

To a solution of methyl (1R,2R)-2-{benzyl[(1R)-1-phenylethyl]amino}-1-hydroxycyclopentanecarboxylate (0.75 g, 2.1 mmol) in methanol (30 mL) was added formic acid (1.44 mL) and 10% Pd/C (0.5 g). The mixture was purged with nitrogen followed by hydrogen and allowed to stir at 40° C. for 3 h under 1 atmosphere of hydrogen. The reaction mixture was then filtered through celite. Hydrochloric acid (1 mL, 12 M) was added to the filtrate, which was then concentrated and chased three times with methanol/benzene (1:1) to afford methyl (1R,2R)-2-amino-1-hydroxycyclopentanecarboxylate as a white solid (0.415 g, 100%). MS: 160.1 (M+H)+

後処理

  1. customThe mixture was purged with nitrogen
  2. filtrationThe reaction mixture was then filtered through celite
  3. additionHydrochloric acid (1 mL, 12 M) was added to the filtrate, which
  4. concentrationwas then concentrated

出典と根拠

ORDレコード
ord-e7c1b6722ab64d769de95297a1047031
出典データセット
uspto-grants-2009_09
特許番号
US07595327B2

反応ノート

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