Sodium Hydroxide → HCID 18768948, compound

HRID 427396Notes

Reaction equation

HRID 427396 reaction equation
[NH:1]1[CH2:5][CH2:4][CH:3]([OH:6])[CH2:2]1.[CH3:7][C:8]([CH3:13])([CH3:12])[CH2:9][CH:10]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>C1COCC1.C(O)(=O)C>[CH3:7][C:8]([CH3:13])([CH3:12])[CH2:9][CH2:10][N:1]1[CH2:5][CH2:4][CH:3]([OH:6])[CH2:2]1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 763353,3-DimethylbutanalHCID 982104-HydroxypyrrolidineHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 18768948HCID 18768948, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

Acetic acid (31 μL), pyrrolidin-3-ol (3.47 g, 39.8 mnol) and 3,3-dimethyl-butyraldehyde (3.99 g, 39.8 mmol) were dissolved in THF (100 mL) and stirred at room temperature for 40 min. The solution was then cooled to 0° C. on an ice bath. To the cold solution sodium triacetoxyborohydride (10.98 g, 51.8 mmol) was added and the mixture was stirred at room temperature overnight. The reaction mixture was basified with a 5.0 M solution of NaOH and extracted with CH2Cl2 (3×150 mL). The organic layer was dried over Na2SO4, filtered and concentrated to dryness to afford 1-(3,3-dimethyl-butyl)-pyrrolidin-3-ol in (6.34 g, 92.5%), which was used without purification.

Workup

  1. temperatureThe solution was then cooled to 0° C. on an ice bath
  2. stirringthe mixture was stirred at room temperature overnight
  3. extractionextracted with CH2Cl2 (3×150 mL)
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-fa372878fb46483abef012e62d0711d2
Source dataset
uspto-grants-2001_11
Patent number
US06313117B1

Reaction notes

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