Sodium borohydride → HCID 70342692, compound

HRID 1081216Notes

Reaction equation

HRID 1081216 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:23]=[CH:22][C:8]([C:9]([NH:11][CH:12]2[CH2:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]2=[O:21])=[O:10])=[CH:7][CH:6]=1.[BH4-].[Na+]>CO>[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:23]=[CH:22][C:8]([C:9]([NH:11][C@@H:12]2[CH2:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C@H:13]2[OH:21])=[O:10])=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 23366111HCID 23366111, compound

Product 1

HCID 70342692HCID 70342692, compoundYield 59.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To an ice-cooled solution/suspension of 2-(4-methoxymethoxybenzamido)-1-indanone (475 mg, 1.5 mmol) in methanol (100 mL) was added NaBH4 (13.9 mg, 3.75 mmol) portionwise. After reaction at rt for 15 min, volatiles were removed in vacuo and the residue triturated in MeOH to afford exclusively trans-2-(4-methoxymethoxybenzamido)-1-indanol as a white solid (279 mg). The mother liquid was chromatographed (silica gel, Hexane:EtOAc/7:1 to 1:1) to afford an additional 82 mg of the product (360 mg in total, 75%).

Workup

  1. customAfter reaction at rt for 15 min
  2. customvolatiles were removed in vacuo
  3. customthe residue triturated in MeOH

Sources & evidence

ORD record
ord-1062c4da7f564a7c9e443caf99d5ffeb
Source dataset
uspto-grants-1996_12
Patent number
US05583221

Reaction notes

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