Methanol → 4-[5-(2,4-Difluoro-phenyl)-4-hydroxymethyl-oxazol-2-yl]-piperidine-1-carboxylic acid benzyl ester

HRID 2288971Notes

Reaction equation

HRID 2288971 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([C:17]2[O:18][C:19]([C:26]3[CH:31]=[CH:30][C:29]([F:32])=[CH:28][C:27]=3[F:33])=[C:20]([C:22](OC)=[O:23])[N:21]=2)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO.[BH4-].[Li+]>CCOCC>[CH2:1]([O:8][C:9]([N:11]1[CH2:12][CH2:13][CH:14]([C:17]2[O:18][C:19]([C:26]3[CH:31]=[CH:30][C:29]([F:32])=[CH:28][C:27]=3[F:33])=[C:20]([CH2:22][OH:23])[N:21]=2)[CH2:15][CH2:16]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 4148881Lithium borohydrideHCID 544076884-[5-(2,4-Difluoro-phenyl)-4-methoxycarbonyl-oxazol-2-yl]-piperidine-1-carboxylic acid benzyl ester

Product 1

HCID 539008614-[5-(2,4-Difluoro-phenyl)-4-hydroxymethyl-oxazol-2-yl]-piperidine-1-carboxylic acid benzyl ester

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a 0.5 liter round bottom flask fitted with a condenser, nitrogen inlet, and mechanical stirrer is added 30.25 g, 66.3 mmoles of 4-[5-(2,4-Difluoro-phenyl)-4-methoxycarbonyl-oxazol-2-yl]-piperidine-1-carboxylic acid benzyl ester, and a mixture of methanol and ether (4 mL to 200 mL). Lithium borohydride 2.17 g (0.1 mol) is added in three portions and then the mixture is stirred and heated to reflux for 30 minutes. The reaction is allowed to cool and carefully quenched with 400 mL of 0.5 N hydrochloric acid. The resulting mixture is extracted with 3×200 mL of methylene chloride. The organics are combined, washed with brine, dried over magnesium sulfate and concentrated to a thick residue to yield the title compound.

Workup

  1. customTo a 0.5 liter round bottom flask fitted with a condenser, nitrogen inlet, and mechanical stirrer
  2. temperatureheated
  3. temperatureto reflux for 30 minutes
  4. temperatureto cool
  5. customcarefully quenched with 400 mL of 0.5 N hydrochloric acid
  6. extractionThe resulting mixture is extracted with 3×200 mL of methylene chloride
  7. washwashed with brine
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated to a thick residue

Sources & evidence

ORD record
ord-ca369f2f5a21473d8021d2800cd97002
Source dataset
uspto-grants-2000_07
Patent number
US06090825

Reaction notes

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