Sodium borohydride → 4-(t-butoxycarbonylamino)-2,2-dimethylbutanol

HRID 1066819Notes

Reaction equation

HRID 1066819 reaction equation
[CH3:1][C:2]1([CH3:15])[CH2:6][CH2:5][N:4]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[C:3]1=[O:14].[BH4-].[Na+]>C(O)C>[C:10]([O:9][C:7]([NH:4][CH2:5][CH2:6][C:2]([CH3:15])([CH3:1])[CH2:3][OH:14])=[O:8])([CH3:13])([CH3:12])[CH3:11]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 108568251,1-Dimethylethyl 3,3-dimethyl-2-oxo-1-pyrrolidinecarboxylate

Product 1

HCID 109659694-(t-butoxycarbonylamino)-2,2-dimethylbutanolYield 93%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3,3-dimethyl-1-(t-butoxycarbonyl)pyrrolidin-2-one (3.35 g, 15.7 mmol) in absolute ethanol under a nitrogen atmosphere was treated with sodium borohydride (1.79 g, 47.1 mmol). The resulting mixture was stirred at ambient tempeature for about 24 hours. The progress of the reaction was monitored by thin layer chromatography. The reaction mixture was concentrated in vacuo. The residue was dissolved in ethyl acetate and washed with sodium bicarbonate. The aqueous fraction was back extracted twice with ethyl acetate. The organic phase was dried over sodium sulfate and concentrated in vacuo. The residue was further purified by chromatography to yield 3.17 grams (93%) of the title intermediate as a clear oil. mp 75.5-76.5° C.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed with sodium bicarbonate
  4. extractionThe aqueous fraction was back extracted twice with ethyl acetate
  5. dry with materialThe organic phase was dried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was further purified by chromatography

Sources & evidence

ORD record
ord-8b6714537f524cac84c8047478e1eacb
Source dataset
uspto-grants-2001_06
Patent number
US06245761B1

Reaction notes

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