Sodium borohydride → Tert-butyl (6-(hydroxymethyl)pyridin-2-yl)carbamate

HRID 1258606Notes

Reaction equation

HRID 1258606 reaction equation
[CH:1]([C:3]1[N:8]=[C:7]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH:6]=[CH:5][CH:4]=1)=[O:2].[BH4-].[Na+]>C1COCC1>[OH:2][CH2:1][C:3]1[N:8]=[C:7]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:14])([CH3:13])[CH3:15])[CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 17832129tert-Butyl (6-formylpyridin-2-yl)carbamate

Product 1

HCID 19349090Tert-butyl (6-(hydroxymethyl)pyridin-2-yl)carbamateYield 73.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of tert-butyl (6-formylpyridin-2-yl)carbamate (13.46 g, 60.57 mmol, 1 eq.) in 200 ml of THF cooled dot 0° C. was added NaBH4 (2.29 g, 60.57 mmol, 1 eq.) portion wise. The reaction was stirred at 0° C. for 1 h and quenched with sat. aqueous NH4Cl. The aqueous layer was extracted with DCM and the organics were combined, dried over MgSO4 and concentrated. The crude residue was purified by chromatography on silica gel to give tert-butyl [6-(hydroxymethyl)pyridin-2-yl]carbamate (9.95 g, 70% yield over 2 steps) as a clear viscous oil.

Workup

  1. customquenched with sat. aqueous NH4Cl
  2. extractionThe aqueous layer was extracted with DCM
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe crude residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-5985475532a24627aaea9a88afbfd603
Source dataset
uspto-grants-2013_06
Patent number
US08466176B2

Reaction notes

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