Sodium borohydride → [2-(Boc-amino)-4-fluoropyridin-3-yl]methanol

HRID 920125

Reaction equation

HRID 920125 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[C:3]=1[CH:16]=[O:17].[BH4-].[Na+]>CO>[F:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:12])[CH3:13])[C:3]=1[CH2:16][OH:17]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 89670239tert-butyl N-(4-fluoro-3-formylpyridin-2-yl)carbamate

Product 1

HCID 89656375[2-(Boc-amino)-4-fluoropyridin-3-yl]methanolYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of the product of step A (480 mg, 2 mmol) in MeOH (3 mL) was added NaBH4 (76 mg, 2 mmol) at 0° C. The reaction was stirred at 0° C. for 30 min. The reaction was quenched with saturated NH4Cl (1 mL) and water (5 mL), extracted with ethyl acetate (2×15 mL). The combined organic phase was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to obtain the title compound (460 mg, 95%) as a white solid which was used directly in the next step. 1H-NMR (600 MHz, DMSO-d6) δ 9.20 (s, 1H), 8.31-8.28 (m, 1H), 7.11-7.09 (m, 1H), 5.26 (t, J=6.0 Hz, 1H), 4.48 (d, J=6.0 Hz, 2H), 1.45 (s, 9H) ppm. MS: M/e 243 (M+1)+.

Workup

  1. customThe reaction was quenched with saturated NH4Cl (1 mL) and water (5 mL)
  2. extractionextracted with ethyl acetate (2×15 mL)
  3. dry with materialThe combined organic phase was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7df23511765b4a218e7f84187555220a
Source dataset
uspto-grants-2016_03
Patent number
US09273046B2

Linked notes

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