Sodium borohydride → (S)-tert-butyl 3-(1-hydroxyethyl)pyrrolidine-1-carboxylate

HRID 57622Notes

Reaction equation

HRID 57622 reaction equation
[C:1]([C@H:4]1[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5]1)(=[O:3])[CH3:2].[BH4-].[Na+]>CO>[OH:3][CH:1]([C@H:4]1[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:13])([CH3:15])[CH3:14])=[O:10])[CH2:5]1)[CH3:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 68071565tert-Butyl (3S)-3-acetylpyrrolidine-1-carboxylate

Product 1

HCID 71113442(S)-tert-butyl 3-(1-hydroxyethyl)pyrrolidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (S)-tert-butyl 3-acetylpyrrolidine-1-carboxylate in methanol (10 mL) was added sodium borohydride (114 mg, 3.0 mmol) at 0° C. The reaction mixture was stirred at ambient temperature for 2 hours then quenched with saturated ammonium chloride solution and extracted with dichloromethane. The combined extracts were dried over magnesium sulfate, filtered, and concentrated to give the title compound for the next step.

Workup

  1. customthen quenched with saturated ammonium chloride solution
  2. extractionextracted with dichloromethane
  3. dry with materialThe combined extracts were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-4fb5d22d6b59418ba567344c09e3fb35
Source dataset
uspto-grants-2016_09
Patent number
US09434726B2

Reaction notes

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