Sodium borohydride → HCID 45083317, compound

HRID 1987750Notes

Reaction equation

HRID 1987750 reaction equation
[C:1]([N:4]1[C@H:8]([C@H:9]([OH:12])CO)[C@@H:7]([OH:13])[CH2:6][NH:5]1)(=[O:3])[CH3:2].I([O-])(=O)(=O)=O.[Na+].[BH4-].[Na+]>C(O)C.O>[C:1]([N:4]1[C@H:8]([CH2:9][OH:12])[C@@H:7]([OH:13])[CH2:6][NH:5]1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 4311764Sodium borohydrideHCID 23667635Sodium periodateHCID 67082071HCID 67082071, compound

Product 1

HCID 45083317HCID 45083317, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
5 °C

Procedure

A solution of 19 (80 mg, 0.42 mmol) in ethanol (5 mL) was added dropwise to a stirred solution of sodium periodate (150 mg, 0.7 mmol) in water (5 mL) at such a rate so as to maintain the reaction temperature at 5° C. On completion, sodium borohydride (135 mg, xs) was added portionwise to the resulting suspension at such a rate so as to maintain the reaction temperature at 0° C. and on complete addition the reaction was allowed to warm to r.t. Flash chromatography grade silica was added to the reaction and the resulting suspension was concentrated in vacuo to afford a white solid. The solid was purified by chromatography to afford 20 (51 mg, 76%) as a colourless oil. 1H NMR δ 4.43 (dd, J=5.7, 3.3 Hz, 1H), 3.91 (q, J=4.7 Hz, 1H), 3.75 (d, J=4.7 Hz, 1H), 3.31 (m, 1H), 3.28 (dd, J=11.8, 5.7 Hz, 1H), 2.75 (dd, J=11.8, 5.5 Hz, 1H), 2.17 (s, 3H). 13C NMR δ 173.9, 76.5, 68.2, 62.5, 55.8, 21.7. HRMS (MH+) calc. for C6H13N2O3: 161.0926. Found 161.0920.

Workup

  1. temperatureto maintain the reaction temperature at 0° C.
  2. additionon complete addition the reaction
  3. temperatureto warm to r.t
  4. additionFlash chromatography grade silica was added to the reaction
  5. concentrationthe resulting suspension was concentrated in vacuo
  6. customto afford a white solid
  7. customThe solid was purified by chromatography

Sources & evidence

ORD record
ord-d0752c92cfdc4df89d7b39eb919edbae
Source dataset
uspto-grants-2009_06
Patent number
US07553839B2

Reaction notes

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