Sodium borohydride → Methyl 2-(hydroxymethyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-4-carboxylate

HRID 1409426Notes

Reaction equation

HRID 1409426 reaction equation
[CH:1]([C:3]1[N:4]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])[CH:5]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[N:7]=1)=[O:2].[BH4-].[Na+]>CO>[OH:2][CH2:1][C:3]1[N:4]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:17])([CH3:19])[CH3:18])[CH:5]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[N:7]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 58638526methyl 2-formyl-1-((2-(trimethylsilyl)-ethoxy)-methyl)-1H-imidazole-4-carboxylate

Product 1

HCID 70980902Methyl 2-(hydroxymethyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-4-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

Into a flask containing a solution of methyl 2-formyl-1-((2-(trimethylsilyl)-ethoxy)-methyl)-1H-imidazole-4-carboxylate (3 g, 10.5 mmol) in MeOH (20 ml), NaBH4 (0.401 g, 10.5 mmol) was added in portions at 0° C. The resulting mixture was allowed to stir at 0° C. for 30 min followed by RT for 1 hour. The reaction mixture was concentrated and the crude was diluted with water and extracted with EtOAc. The organic layer was concentrated under reduced pressure. Yield 1.5 g. LC-MS: [M+1]=287.17.

Workup

  1. additionwas added in portions at 0° C
  2. waitfollowed by RT for 1 hour
  3. concentrationThe reaction mixture was concentrated
  4. additionthe crude was diluted with water
  5. extractionextracted with EtOAc
  6. concentrationThe organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-5343b9fe06724720a7c313978e2712a2
Source dataset
uspto-grants-2014_12
Patent number
US08921378B2

Reaction notes

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