(1S,3R)-1-(Boc-amino)-3-(Cbz-amino)cyclopentane → 1,1-Dimethylethyl N-[(1S,3R)-3-aminocyclopentyl]carbamate

HRID 1257636Notes

Reaction equation

HRID 1257636 reaction equation
[C:1]([O:5][C:6](=[O:24])[NH:7][C@H:8]1[CH2:12][CH2:11][C@@H:10]([NH:13]C(OCC2C=CC=CC=2)=O)[CH2:9]1)([CH3:4])([CH3:3])[CH3:2]>C(O)C.[Pd]>[C:1]([O:5][C:6](=[O:24])[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

4

Reactant 1

HCID 67351544(1S,3R)-1-(Boc-amino)-3-(Cbz-amino)cyclopentane

Product 1

HCID 517769401,1-Dimethylethyl N-[(1S,3R)-3-aminocyclopentyl]carbamateYield 102.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of ((1S,3R)-3-benzyloxycarbonylamino-cyclopentyl)-carbamic acid tert-butyl ester (635 mg, 1.90 mmol) and 10% Pd on carbon (202 mg, 0.19 mmol) in ethanol (15 mL) was stirred at ambient temperature under an atmosphere of hydrogen for 16 hours. The reaction mixture was filtered through Celite® which was washed with ethanol and the filtrate concentrated under vacuum to afford 390 mg (quant.) of ((1S,3R)-3-amino-cyclopentyl)-carbamic acid tert-butyl ester as a colorless oil. LCMS (Method H, ESI): RT=0.38 min, m+H=200.9; 1H NMR (400 MHz, DMSO) δ: 6.82 (d, 1H), 3.75-3.66 (m, 1H), 3.17 (m, 2H), 1.98 (m, 1H), 1.70 (m, 3H), 1.49 (m, 1H), 1.37 (s, 9H), 1.31 (m, 1H), 1.14 (m, 1H).

Workup

  1. filtrationThe reaction mixture was filtered through Celite® which
  2. washwas washed with ethanol
  3. concentrationthe filtrate concentrated under vacuum

Sources & evidence

ORD record
ord-1f3d2cda223a4b70b8decc6f6d45df2c
Source dataset
uspto-grants-2013_06
Patent number
US08461328B2

Reaction notes

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