Sodium borohydride → HCID 118276758, compound

HRID 530646Notes

Reaction equation

HRID 530646 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][O:11][C@H:10]([C:14]([C:16]2[CH:17]=[N:18][C:19]([O:22][CH3:23])=[CH:20][CH:21]=2)=[O:15])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>CO>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][O:11][C@H:10]([CH:14]([OH:15])[C:16]2[CH:17]=[N:18][C:19]([O:22][CH3:23])=[CH:20][CH:21]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 118276731HCID 118276731, compound

Product 1

HCID 118276758HCID 118276758, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

(S)-2-(6-Methoxy-pyridine-3-carbonyl)-morpholine-4-carboxylic acid tert-butyl ester (305 mg, 0.95 mmol) was dissolved in methanol (5 mL) and cooled to 0° C. Sodium borohydride (36 mg, 0.95 mmol) was added and the resulting reaction mixture was stirred for 2 h at room temperature before pouring onto NaHCO3 and extracting 3 times with ethyl acetate. The combined organic phase was washed with brine, dried over MgSO4, filtered and concentrated to afford (S)-2-[hydroxy-(6-methoxy-pyridin-3-yl)-methyl]-morpholine-4-carboxylic acid tert-butyl ester (295 mg, 96%) as a colorless solid.

Workup

  1. customthe resulting reaction mixture
  2. additionbefore pouring onto NaHCO3
  3. extractionextracting 3 times with ethyl acetate
  4. washThe combined organic phase was washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-6737af898e854597a5e3e29198f324a7
Source dataset
uspto-grants-2016_05
Patent number
US09353096B2

Reaction notes

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