Benzyl Alcohol → HCID 23535587, compound

HRID 2115330Notes

Reaction equation

HRID 2115330 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:5](C(O)=O)=[CH:4][N:3]=1.CC[N:13]([CH:17](C)C)C(C)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:27])C=CC=CC=1.[CH2:37]([OH:44])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>C1(C)C=CC=CC=1.O.C(OCC)(=O)C>[CH2:37]([O:44][C:17](=[O:27])[NH:13][C:5]1[CH:4]=[N:3][C:2]([CH3:1])=[CH:10][CH:9]=1)[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1

Participants

8

Reactant 4

HCID 244Benzyl AlcoholHCID 81531DiisopropylethylamineHCID 1378606-Methylnicotinic acidHCID 199401P,P-Diphenylphosphinic azide

Product 1

HCID 23535587HCID 23535587, compoundYield 59.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 6-methylnicotinic acid (36.4 mmol) in toluene (100 mL) was added DIPEA (120 mmol) and Diphenylphosphoryl azide (91.1 mmol). The reaction mixture was heated to reflux for 1 h, cooled to RT and treated with benzyl alcohol (120 mmol). After 30 min ethyl acetate (200 mL) and water (200 mL) were added, the layers were separated and the organic layer washed with water (3×100 mL). The solvents were removed in vacuo and the residue was purified by preparative HPLC chromatography to give (6-methyl-pyridin-3-yl)-carbamic acid benzyl ester (5.2 g, 21.5 mmol, 59%) as a colourless oil.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 1 h
  3. customthe layers were separated
  4. washthe organic layer washed with water (3×100 mL)
  5. customThe solvents were removed in vacuo
  6. customthe residue was purified by preparative HPLC chromatography

Sources & evidence

ORD record
ord-1f05a40436fb43708d7d2f074e365f02
Source dataset
uspto-grants-2008_10
Patent number
US07435815B2

Reaction notes

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