Dimethylbarbituric acid → Tert-butyl n-((1r,3r)-3-aminocyclopentyl)carbamate

HRID 1257633노트

반응식

HRID 1257633 반응식
[C:1]([O:5][C:6](=[O:20])[NH:7][C@@H:8]1[CH2:12][CH2:11][C@@H:10]([NH:13]C(OCC=C)=O)[CH2:9]1)([CH3:4])([CH3:3])[CH3:2].CN1C(=O)CC(=O)N(C)C1=O>C(Cl)Cl.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:1]([O:5][C:6](=[O:20])[NH:7][C@@H:8]1[CH2:12][CH2:11][C@@H:10]([NH2:13])[CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

참가 물질

5

반응물 2

HCID 69860Dimethylbarbituric acidHCID 67352799((1R,3R)-3-allyloxycarbonylamino-cyclopentyl)-carbamic acid tert-butyl ester

생성물 1

HCID 51776938Tert-butyl n-((1r,3r)-3-aminocyclopentyl)carbamate수율 56%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 6344Dichloromethane용매

실험 절차

A mixture of ((1R,3R)-3-allyloxycarbonylamino-cyclopentyl)-carbamic acid tert-butyl ester (890 mg, 3.13 mmol), 1,3-dimethylbarbituric acid (1.47 g, 9.39 mmol) and Pd(PPh3)4 (181 mg, 0.15 mmol) in DCM (30 mL) was stirred at ambient temperature for 90 minutes. The reaction mixture was concentrated under vacuum and purified by column chromatography on silica gel (gradient: 2M NH3 in methanol solution in DCM) to afford 350 mg (56%) ((1R,3R)-3-amino-cyclopentyl)-carbamic acid tert-butyl ester. LCMS (Method H, ESI): RT=0.36 min, m+H=200.9; 1H NMR (400 MHz, DMSO) δ: 6.77 (s, 1H), 3.90 (m, 1H), 3.31 (m, 1H), 1.87 (m, 2H), 1.54 (m, 2H), 1.37 (s, 10H), 1.18 (m, 1H).

후처리

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. custompurified by column chromatography on silica gel (gradient: 2M NH3 in methanol solution in DCM)

출처 및 근거

ORD 기록
ord-4837189bccea43d3afaf8705b62fadbb
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08461328B2

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