MAGNESIUM SILICATE (synthetic) → (6-Amino-indan-1-yl)-carbamic acid tert-butyl ester

HRID 2053723Notes

Reaction equation

HRID 2053723 reaction equation
[C:1]([O:5][C:6](=[O:20])[NH:7][CH:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([N+:17]([O-])=O)[CH:15]=2)[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[O-][Si]([O-])=O.[Mg+2]>CO.Cl[Cu]>[C:1]([O:5][C:6](=[O:20])[NH:7][CH:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([NH2:17])[CH:15]=2)[CH2:10][CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 61680MAGNESIUM SILICATE (synthetic)HCID 69224563HCID 69224563, compound

Product 1

HCID 69224271(6-Amino-indan-1-yl)-carbamic acid tert-butyl esterYield 73%

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 887MethanolSolvent

Procedure

Add KBH4 (1.59 g, 29.4 mmol) slowly to a mixture of (6-nitro-indan-1-yl)carbamic acid tert-butyl ester (1.17 g, 4.2 mmol) and CuCl (1.25 g, 12.6 mmol) in 50 mL of methanol at 0° C. over 15 min. Stir the mixture for 1 h and then pass through a Florisil pad. Evaporate the THF and dissolve the solid in EtOAc. Wash the mixture with water, dry, and concentrate to afford 0.76 g (73%) of (6-aminoindan-1-yl)carbamic acid tert-butyl ester. 1H NMR (CDCl3) d 6.99 (1H, d, J=8.0 Hz), 6.65 (1H, s), 6.56 (1H, dd, J=8.0 and 2.0 Hz), 5.09 (1H, q, J=8.0 Hz), 4.70 (1H, br d, J=7.2 Hz), 3.60 (2H, s), 2.86-2.79 (1H, m), 2.75-2.67 (1H, m), 2.58-2.47 (1H, m), 1.78-1.69 (1H, m), 1.48 (3H, s). 2.86-2.79 (1H, m), 2.75-2.67 (1H, m), 2.58-2.47 (1H, m), 1.78-1.69 (1H, m), 1.48 (3H, s).

Workup

  1. customEvaporate the THF
  2. dissolutiondissolve the solid in EtOAc
  3. washWash the mixture with water
  4. customdry
  5. concentrationconcentrate

Sources & evidence

ORD record
ord-e03793b668eb465a85a9ffabec204473
Source dataset
uspto-grants-2008_02
Patent number
US07326731B2

Reaction notes

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