Sodium borohydride → [1-(tert-Butyl-dimethyl-silanyl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-5-yl]-methanol

HRID 1994193Notes

Reaction equation

HRID 1994193 reaction equation
[C:1]([Si:5]([CH3:18])([CH3:17])[N:6]1[C:10]2=[N:11][CH:12]=[C:13]([CH:15]=[O:16])[CH:14]=[C:9]2[CH2:8][CH2:7]1)([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>CCO>[C:1]([Si:5]([CH3:18])([CH3:17])[N:6]1[C:10]2=[N:11][CH:12]=[C:13]([CH2:15][OH:16])[CH:14]=[C:9]2[CH2:8][CH2:7]1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 587309341-(tert-Butyl-dimethyl-silanyl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde

Product 1

HCID 58730943[1-(tert-Butyl-dimethyl-silanyl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-5-yl]-methanolYield 24%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred and cooled (0° C.) solution of crude 13 (2.77 g, 10.6 mmol) in EtOH (100 mL) was added NaBH4 (0.48 mg, 12.7 mmol) in a single portion. The mixture was allowed to warm to r.t. After 20 h the mixture was concentrated and partitioned between CH2Cl2-brine. The organic layer was dried (MgSO4) and concentrated. The residue was purified by SGC with CH2Cl2:MeOH as eluent (gradient up to 5% MeOH) to afford alcohol 14 (0.67 g, 24%). 1H NMR (400 MHz; CDCl3) δ 0.31 (s, 6H), 0.94 (s, 9H), 2.97 (t, J=8.2 Hz, 2H), 3.65 (t, J=8.2 Hz, 2H), 4.39 (s, 2H), 7.19 (s, 1H), 7.69 (s, 1H).

Workup

  1. concentrationAfter 20 h the mixture was concentrated
  2. custompartitioned between CH2Cl2-brine
  3. dry with materialThe organic layer was dried (MgSO4)
  4. concentrationconcentrated
  5. customThe residue was purified by SGC with CH2Cl2

Sources & evidence

ORD record
ord-59b802faf0e6440d88be4b4a1e68aa87
Source dataset
uspto-grants-2010_01
Patent number
US07652137B2

Reaction notes

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