Benzyl Alcohol → HCID 11152485, compound

HRID 1295822Notes

Reaction equation

HRID 1295822 reaction equation
[O:1]=[C:2]1[CH2:6][CH:5]([CH2:7][CH2:8][CH3:9])[CH2:4][N:3]1[CH2:10][N:11]1[C:15](C(O)=O)=[CH:14][N:13]=[CH:12]1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:26])C=CC=CC=1.N#N.[CH2:38]([OH:45])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1.CC[N:48]([CH2:51]C)CC>C1(C)C=CC=CC=1>[O:1]=[C:2]1[CH2:6][CH:5]([CH2:7][CH2:8][CH3:9])[CH2:4][N:3]1[CH2:10][N:11]1[C:15]([NH:48][C:51](=[O:26])[O:45][CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)=[CH:14][N:13]=[CH:12]1

Participants

7

Reactant 5

HCID 244Benzyl AlcoholHCID 947NitrogenHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 58911253HCID 58911253, compound

Product 1

HCID 11152485HCID 11152485, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
90 °C

Procedure

In a three necked flask, under argon, a solution of 1-[(2-oxo-4-propylpyrrolidin-1-yl)methyl]-1H-imidazole-5-carboxylic acid a32 (0.35 g, 1.39 mmol, predried by azeotropic distillation with toluene), diphenylphosphoryl azide (0.58 g, 2.1 mmol) and Et3N (0.29 ml) in toluene (5 ml) is heated at 40° C. with formation of N2. The temperature is kept at 40° C. for 4 h and benzyl alcohol (0.301 g, 0.21 mmol) is added. The solution is heated at 90° C. for 1 h, cooled down to room temperature, stirred 48 h, heated at 90° C. for 1 h and concentrated in vacuo. The crude carbamate is purified by chromatography on silicagel (CH2Cl2/MeOH) to afford benzyl 1-[(2-oxo-4-propylpyrrolidin-1-yl)methyl]-1H-imidazol-5-ylcarbamate 83 (0.011 g) as an off white solid.

Workup

  1. temperaturecooled down to room temperature
  2. temperatureheated at 90° C. for 1 h
  3. concentrationconcentrated in vacuo
  4. customThe crude carbamate is purified by chromatography on silicagel (CH2Cl2/MeOH)

Sources & evidence

ORD record
ord-3bc3e1300a4f4a718739144062c4cceb
Source dataset
uspto-grants-2007_07
Patent number
US07244747B2

Reaction notes

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