Sodium borohydride → HCID 24752610, compound

HRID 253084Notes

Reaction equation

HRID 253084 reaction equation
[Br-].[CH2:2]([N+:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH3:21])=[C:11]([CH2:22][O:23][CH2:24][C:25]2[CH:30]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:28]=[C:27]([C:35]([F:38])([F:37])[F:36])[CH:26]=2)[CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[BH4-].[Na+]>C(O)C>[CH2:2]([N:9]1[CH2:10][C:11]([CH2:22][O:23][CH2:24][C:25]2[CH:30]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:28]=[C:27]([C:35]([F:36])([F:37])[F:38])[CH:26]=2)=[C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH3:21])[CH2:13][CH2:14]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydride2×HCID 86615506HCID 86615506, compound

Product 1

HCID 24752610HCID 24752610, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
35 °C

Procedure

A solution of 1-benzyl-3-(3,5-bis-trifluoromethyl-benzyloxymethyl)-4-o-tolyl-pyridinium bromide (163 mg, 0.273 mmol) in 6 ml of ethanol was added sodium borohydride (10 mg, 0.26 mmol) at 0° C. The mixture was heated to 35° C. and stirred at this temperature over night. Another portion of sodium borohydride (10 mg, 0.26 mmol) was added and the mixture was heated to 50° C. for 2 h. After cooling to room temperature and quenching with water the mixture was diluted with a saturated aqueous solution of sodium carbonated and extracted with three portions of tert-butyl methyl ether. The combined organic layers were dried over sodium sulfate and concentrated in vacuo. Flash column chromatography gave 78 mg (55%) of the title compound as a light yellow oil.

Workup

  1. temperaturethe mixture was heated to 50° C. for 2 h
  2. temperatureAfter cooling to room temperature
  3. customquenching with water the mixture
  4. additionwas diluted with a saturated aqueous solution of sodium
  5. extractionextracted with three portions of tert-butyl methyl ether
  6. dry with materialThe combined organic layers were dried over sodium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-033284270ff04e04bb16fefc6a3a3a24
Source dataset
uspto-grants-2011_01
Patent number
US07872022B2

Reaction notes

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