Triethylamine → HCID 9813361, compound

HRID 983680Notes

Reaction equation

HRID 983680 reaction equation
C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:8])C=CC=CC=1.C([N:20]([CH2:23]C)CC)C.[CH2:25]([C@:32]1([CH2:38]C(O)=O)[CH2:36][CH2:35][C@@H:34]([CH3:37])[CH2:33]1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C1(C)C=CC=CC=1.C(OCC)(=O)C>[N:20]([CH2:38][C@@:32]1([CH2:25][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH2:36][CH2:35][C@@H:34]([CH3:37])[CH2:33]1)=[C:23]=[O:8]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 58626983HCID 58626983, compound

Product 1

HCID 9813361HCID 9813361, compoundYield 100.6%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Diphenylphosphoryl azide (4.48 g, 16 mmol), triethylamine (1.69 g, 16.8 mmol), and acid ((1S,3R)-1-benzyl-3-methyl-cyclopentyl)-acetic acid (3.74 g, 16 mmol) were refluxed in toluene (40 mL) for 17 hours. The mixture was allowed to cool and then taken up in ethyl acetate (150 mL), washed with saturated aqueous sodium hydrogen carbonate (200 mL), brine (150 mL), and dried (MgSO4). The solvent was removed under reduced pressure to give 3.69 g (100%) of ((1S,3R)-1-isocyanatomethyl-3-methyl-cyclopentylmethyl)-benzene, which was used without further purification;

Workup

  1. temperatureto cool
  2. washwashed with saturated aqueous sodium hydrogen carbonate (200 mL), brine (150 mL)
  3. dry with materialdried (MgSO4)
  4. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-398fdd10cb394954b76c1217f41dc017
Source dataset
uspto-grants-2005_03
Patent number
US06864390B2

Reaction notes

Loading…