tert-Butyl ethyl(4-(5-nitro-1H-indol-3-yl)cyclohex-3-enyl)carbamate → tert-Butyl 4-(5-amino-1H-indol-3-yl)cyclohexyl(ethyl)carbamate

HRID 2043524Notes

Reaction equation

HRID 2043524 reaction equation
[CH2:1]([N:3]([CH:11]1[CH2:16][CH2:15][C:14]([C:17]2[C:25]3[C:20](=[CH:21][CH:22]=[C:23]([N+:26]([O-])=O)[CH:24]=3)[NH:19][CH:18]=2)=[CH:13][CH2:12]1)[C:4](=[O:10])[O:5][C:6]([CH3:9])([CH3:8])[CH3:7])[CH3:2]>N.CO.[Pd]>[NH2:26][C:23]1[CH:24]=[C:25]2[C:20](=[CH:21][CH:22]=1)[NH:19][CH:18]=[C:17]2[CH:14]1[CH2:13][CH2:12][CH:11]([N:3]([CH2:1][CH3:2])[C:4](=[O:10])[O:5][C:6]([CH3:7])([CH3:8])[CH3:9])[CH2:16][CH2:15]1

Participants

5

Reactant 1

HCID 57474461tert-Butyl ethyl(4-(5-nitro-1H-indol-3-yl)cyclohex-3-enyl)carbamate

Product 1

HCID 57474462tert-Butyl 4-(5-amino-1H-indol-3-yl)cyclohexyl(ethyl)carbamateYield 84.3%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 222AmmoniaSolventHCID 887MethanolSolvent

Procedure

A solution of compound 118 (0.55 g, 1.427 mmol) in 2 M NH3 in methanol (10 mL) was treated with Pd—C (0.05 g) and flushed with hydrogen gas. The reaction was stirred at room temperature overnight (16 h) under hydrogen atmosphere (balloon pressure). The solution was filtered through a celite bed using methanol washes (2×10 mL). The solvent was evaporated and crude was purified by column chromatography (2 M NH3 in methanol: CH2Cl2, 2.5:97.5) to obtain compound 119 (0.43 g, 84%) as a solid in 2:3 ratio of diastereomers. 1H NMR (DMSO-d6) δ: 0.99, 1.07 (2t, 3H, J=7.2, 6.6 Hz), 1.37-1.51 (m, 11H), 1.63-1.78 (m, 4H), 2.01-2.18 (m, 2H), 2.98-3.04 (m, 1H), 3.11-3.17 (m, 2H), 3.68-3.80 (m, 1H), 4.52 (brs, 2H), 6.44-6.47 (m, 1H), 6.66-6.70 (m, 1H), 6.86-6.88, 6.99-7.06 (2m, 2H), 10.23, 10.27 (2s, 1H); ESI-MS m/z (%): 380 (M+Na, 6), 358 (MH+, 5), 302 (100), 258 (54); ESI-HRMS calculated for C21H32N3O2 (MH+), Calculated: 358.2507; Observed: 358.2489.

Workup

  1. customflushed with hydrogen gas
  2. filtrationThe solution was filtered through a celite bed
  3. customThe solvent was evaporated
  4. customcrude was purified by column chromatography (2 M NH3 in methanol: CH2Cl2, 2.5:97.5)

Sources & evidence

ORD record
ord-7b4cdcfcad2b49e28c368b2a6567cd52
Source dataset
uspto-grants-2013_11
Patent number
US08586620B2

Reaction notes

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