Sodium borohydride → HCID 11252928, compound

HRID 1921074Notes

Reaction equation

HRID 1921074 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([C@H:13]([OH:16])CO)[C@@H:10]([OH:17])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].I([O-])(=O)(=O)=O.[Na+].[BH4-].[Na+]>C(O)C.O>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([CH2:13][OH:16])[C@@H:10]([OH:17])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 4311764Sodium borohydrideHCID 11402367HCID 11402367, compoundHCID 23667635Sodium periodate

Product 1

HCID 11252928HCID 11252928, compoundYield 92.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

N-tert-Butoxycarbonyl-(3R,4S)-3-hydroxy-4-[(1S)-1,2-dihydroxyethyl]pyrrolidine (3.4 g, 13.7 mmol) in ethanol (50 mL) was added dropwise to a stirred solution of sodium periodate (3.4 g, 16 mmol) in water (25 mL) while maintaining the reaction temperature at 0° C. The reaction was left an additional 20 min after which time sodium borohydride (2.0 g, excess) was added portionwise while again ensuring the reaction temperature was maintained at 0° C. On complete addition the solid was filtered, washed with ethanol (50 mL) and concentrated in vacuo to afford a syrup. Chromatography afforded 1 (2.74 g, 92%) as a syrup.

Workup

  1. additionwas added portionwise
  2. temperaturewas maintained at 0° C
  3. additionOn complete addition the solid
  4. filtrationwas filtered
  5. washwashed with ethanol (50 mL)
  6. concentrationconcentrated in vacuo
  7. customto afford a syrup

Sources & evidence

ORD record
ord-4aabe1f49a0b4b379569dda14138faf7
Source dataset
uspto-grants-2012_05
Patent number
US08173662B2

Reaction notes

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