Methanol → HCID 11008674, compound

HRID 1953801Notes

Reaction equation

HRID 1953801 reaction equation
C1COCC1.[C:6]1([C:12]([C:14]2[N:18]([CH3:19])[N:17]=[CH:16][CH:15]=2)=[O:13])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.CO>C1(C)C=CC=CC=1>[C:6]1([C@H:12]([C:14]2[N:18]([CH3:19])[N:17]=[CH:16][CH:15]=2)[OH:13])[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 8028TetrahydrofuranHCID 11789926(1-Methyl-1H-pyrazol-5-yl)(phenyl)methanone

Product 1

HCID 11008674HCID 11008674, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
-10 °C

Procedure

To a solution of (R)-3,3-diphenyl-1-methylpyrrolidine[1,2-c]-1,3,2-oxazaborole 1M in toluene (7.5 ml, 7.5 mmol) cooled to -10° C., under an argon atmosphere, a solution of catecolborane 1M in THF (100 ml, 100 mmol) is added dropwise. To the resulting mixture a solution of phenyl-(1-methyl-1H-pyrazol-5-yl)ketone, III (9.30 g, 50 mmol) in dry toluene is added. Once the addition has been completed the mixture is stirred for 1 hour at -10° C. and then over night at room temperature. Next, MeOH (10 ml) is carefully added while stirring, which is maintained for 6 hours. The reaction mixture is concentrated to half the volume, washed successively with water and with a solution of saturated NaCl, dried and the solvent evaporated to yield an oil which is purified on a silicagel column, eluted with a mixture of ethyl acetate: petrol ether (7:3) to give (R)-(+)-phenyl-(1-methyl-1H-pyrazol-5-yl)methanol, (+)-II (7.82 g, 83%), whose optical purity as determined by chiral HPLC is 99%. M.p. 81-83° C.; [α]D =+16.6 (c=1.0, CHCl3).

Workup

  1. additionOnce the addition
  2. waitover night at room temperature
  3. stirringwhile stirring
  4. temperaturewhich is maintained for 6 hours
  5. concentrationThe reaction mixture is concentrated to half the volume
  6. washwashed successively with water and with a solution of saturated NaCl
  7. customdried
  8. customthe solvent evaporated
  9. customto yield an oil which
  10. customis purified on a silicagel column
  11. washeluted with a mixture of ethyl acetate: petrol ether (7:3)

Sources & evidence

ORD record
ord-42d5e544593b45baa2a6bf7da179f1a1
Source dataset
uspto-grants-2000_09
Patent number
US06118009

Reaction notes

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