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

HRID 736808노트

반응식

HRID 736808 반응식
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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 887Methanol용매

반응 조건

온도
40 °C

실험 절차

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)+

후처리

  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

출처 및 근거

ORD 기록
ord-e7c1b6722ab64d769de95297a1047031
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07595327B2

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