Trifluoroacetic acid → (3aR,5R,6aR)-Methyl 2-benzyl-5-((tert-butoxycarbonyl)amino)octahydro-cyclopenta[c]pyrrole-3a-carboxylate

HRID 571350노트

반응식

HRID 571350 반응식
[CH3:1][O:2][C:3]([C:5]1[CH2:9][C@H:8]([NH:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH:6]=1)=[O:4].CO[CH2:20][N:21]([CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH2:22][Si](C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:27]([N:21]1[CH2:22][C@@:5]2([C:3]([O:2][CH3:1])=[O:4])[CH2:9][C@H:8]([NH:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][C@H:6]2[CH2:20]1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

참가 물질

5

반응물 3

HCID 6422Trifluoroacetic acidHCID 353442Benzyl(methoxymethyl)((trimethylsilyl)methyl)amineHCID 10586185methyl (4R)-4-{[(tert-butoxy)carbonyl]amino}cyclopent-1-ene-1-carboxylate

생성물 1

HCID 86708893(3aR,5R,6aR)-Methyl 2-benzyl-5-((tert-butoxycarbonyl)amino)octahydro-cyclopenta[c]pyrrole-3a-carboxylate

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a solution of the product from Step B (5.51 g, 20 mmol) and N-(methoxymethyl)-N-(trimethylsilylmethyl)benzylamine (6.4 mL, 24 mmol, Aldrich) in DCM (40 mL) was added 1M TFA in DCM (2.4 mL, 2.4 mmol) slowly. The resulting mixture was stirred at rt overnight and quenched by the addition of saturated aqueous NaHCO3 solution. The organic phase was washed with brine, dried over Na2SO4. Evaporation and purification by column chromatography (eluent: 10% EtOAc in hexanes to 20%) gave the desired isomer as a colorless gel. 1H-NMR (400 MHz, CDCl3) of the desired isomer: δ 1.38 (s, 9H), 1.66-1.86 (m, 2H), 1.86-1.96 (m, 1H), 1.96-2.08 (m, 1H), 2.29-2.63 (m, 3H), 2.71-2.93 (m, 2H), 3.43-3.56 (m, 2H), 3.58-3.74 (s, 3H), 4.08-4.29 (m, 1H), 4.78 (d, J=6.6 Hz, 1H), 7.11-7.31 (m, 5H). LC/MS: C24H28N2O4: m/z 375.2 (M+H).

후처리

  1. customquenched by the addition of saturated aqueous NaHCO3 solution
  2. washThe organic phase was washed with brine
  3. dry with materialdried over Na2SO4
  4. customEvaporation and purification by column chromatography (eluent: 10% EtOAc in hexanes to 20%)
  5. customgave the desired isomer as a colorless gel

출처 및 근거

ORD 기록
ord-d3fa2e254a6c46fe8a5b9f317cd57b4a
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09024017B2

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