Triethylamine → HCID 69622402, compound

HRID 2191081Notes

Reaction equation

HRID 2191081 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH:13]2[CH2:14][CH2:15][CH:9]1[CH2:10][NH:11][CH2:12]2)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl[C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18].C(N(CC)CC)C>C(Cl)Cl>[CH:9]12[N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH:13]([CH2:14][CH2:15]1)[CH2:12][N:11]([C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18])[CH2:10]2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 157409088-Boc-3,8-diaza-bicyclo(3.2.1)octane

Product 1

HCID 69622402HCID 69622402, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 8-tert-butoxycarbonyl-3,8-diazabicyclo[3.2.1]octane (238 mg, 1.12 mmol), benzyl chloroformate (160 μL, 1.12 mmol) and triethylamine (280 μL, 2.0 mmol) in DCM (20 mL) was stirred at room temperature for 22 h. The reaction mixture was diluted with DCM (20 mL) and washed with water (25 mL). The organic phase was dried (magnesium sulfate) and the solvent was removed in vacuo to give the title compound (336 mg, 87%) as a clear oil. δH (DMSO-d6) 7.45-7.28 (5H, m), 5.17-5.03 (2H, m), 4.18-4.06 (2H, m), 3.79-3.69 (2H, m), 3.10-2.90 (2H, m), 1.85-1.72 (2H, m), 1.60-1.49 (2H, m), 1.41 (9H, s).

Workup

  1. washwashed with water (25 mL)
  2. dry with materialThe organic phase was dried (magnesium sulfate)
  3. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-be779d3a50984bcaa50f7e37ba706578
Source dataset
uspto-grants-2012_12
Patent number
US08324204B2

Reaction notes

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