Triethylamine → HCID 72238040, compound

HRID 2370301Notes

Reaction equation

HRID 2370301 reaction equation
[CH2:1]1[O:14][C:4]2([CH2:11][CH2:10][CH:9]3[CH2:12][CH:5]2[CH2:6][CH2:7][CH:8]3[NH2:13])[O:3][CH2:2]1.C(N(CC)CC)C.[CH2:22]([O:29][C:30](Cl)=[O:31])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>ClCCl.O>[CH2:2]1[O:3][C:4]2([CH2:11][CH2:10][CH:9]3[CH2:12][CH:5]2[CH2:6][CH2:7][CH:8]3[NH:13][C:30]([O:29][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:31])[O:14][CH2:1]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 72238032HCID 72238032, compound

Product 1

HCID 72238040HCID 72238040, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

1.97 g of 6-Amino-bicyclo[3.3.1]nonan-2-one ethylene ketal (98) were dissolved in 30 mL of dry dichloromethane and 1.52 mL of dry triethylamine and 1.42 mL of benzylchloroformate were added. The mixture was stirred overnight, taken up in water and extracted three times with ethyl acetate. The combined organic layer was dried over sodium sulfate and evaporated to dryness. The crude product was purified by chromatography to give 0.92 g of the desired product. Rt=3.18 min (Method E). Detected mass: 332.2 (M+H+).

Workup

  1. extractionextracted three times with ethyl acetate
  2. dry with materialThe combined organic layer was dried over sodium sulfate
  3. customevaporated to dryness
  4. customThe crude product was purified by chromatography

Sources & evidence

ORD record
ord-5fd275a78d39462c993779ec4ef88bcc
Source dataset
uspto-grants-2014_04
Patent number
US08710077B2

Reaction notes

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