Triethylamine → HCID 67355543, compound

HRID 627378Notes

Reaction equation

HRID 627378 reaction equation
[CH2:1]([N:8]1[CH2:15][CH:14]2[NH:16][CH:10]([CH2:11][CH2:12][CH2:13]2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:17]([O:21][C:22](=O)[O:23]C(C)(C)C)([CH3:20])([CH3:19])[CH3:18].C(N(CC)CC)C>C(Cl)Cl>[C:17]([O:21][C:22]([N:16]1[CH:14]2[CH2:13][CH2:12][CH2:11][CH:10]1[CH2:9][N:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH2:15]2)=[O:23])([CH3:20])([CH3:19])[CH3:18]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10219638Carbonic acid, bis(1,1-dimethylethyl) esterHCID 4965795692373-56-3

Product 1

HCID 67355543HCID 67355543, compoundYield 43.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
23 °C

Procedure

To a solution of 3-benzyl-3,9-diaza-bicyclo[3.3.1]nonane (755 mg, 3.49 mmol, 1.0 eq) in CH2Cl2 (10 mL) was added di-tert-butylcarbonate (990 mg, 4.54 mmol, 1.3 eq) and triethylamine (0.730 mL, 5.24 mmol, 1.5 eq) and the mixture stirred for 16 hours at 23° C. The reaction mixture was diluted with CH2Cl2 and washed with water. The organic was collected and dried (Na2SO4), filtered, and concentrated to an oil. The crude was purified using silica gel chromatography eluting with ethyl acetate/heptane mixtures which gave the desired product as a colorless oil (477 mg) in 41% yield. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.48 (s, 9H) 1.51-1.64 (m, 1H) 1.64-1.75 (m, 2H) 1.75-1.93 (m, 2H) 2.21-2.39 (m, 2H) 2.79-2.92 (m, 3H) 3.40 (s, 2H) 4.06 (br. s., 1H) 4.18 (br. s., 1H) 7.21-7.30 (m, 1H) 7.34 (d, J=4.55 Hz, 4H).

Workup

  1. washwashed with water
  2. customThe organic was collected
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated to an oil
  6. customThe crude was purified
  7. washeluting with ethyl acetate/heptane mixtures which

Sources & evidence

ORD record
ord-a5c40042e245402b81c7420798385b8d
Source dataset
uspto-grants-2016_04
Patent number
US09309252B2

Reaction notes

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