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

HRID 1257633Notes

Reaction equation

HRID 1257633 reaction equation
[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]

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-4837189bccea43d3afaf8705b62fadbb
Source dataset
uspto-grants-2013_06
Patent number
US08461328B2

Reaction notes

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