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

HRID 1257633ノート

反応式

HRID 1257633 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-4837189bccea43d3afaf8705b62fadbb
出典データセット
uspto-grants-2013_06
特許番号
US08461328B2

反応ノート

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