Tetrahydrofuran → tert-Butyl 3-(hydroxymethyl)pyrrolidine-1-carboxylate

HRID 72416Notes

Reaction equation

HRID 72416 reaction equation
[C:1]([N:8]1[CH2:12][CH2:11][CH:10]([C:13](O)=[O:14])[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].O1CCCC1>C([O-])(O)=O.[Na+]>[OH:14][CH2:13][CH:10]1[CH2:11][CH2:12][N:8]([C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[CH2:9]1

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 27605291-((Tert-butoxy)carbonyl)pyrrolidine-3-carboxylic acid

Product 1

HCID 5237175tert-Butyl 3-(hydroxymethyl)pyrrolidine-1-carboxylateYield 109.2%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

To an ice cooled solution of 1-Boc-pyrrolidine-3-carboxylic acid (1 g, 4.64 mmol) in dry tetrahydrofuran (6 ml) Borane-methyl sulfide complex (2M in tetrahydrofuran) (3.48 ml, 6.96 mmol) was added dropwise the under N2 atmosphere The reaction mixture was stirred overnight at room temperature. NaHCO3 sat. sol. (20 ml) was added and the resulting mixture was stirred for 30 min. The mixture was extracted with ethylacetate (3×20 ml). Collected organics after solvent evaporation afforded the title compound (D39) (1.02 g)

Workup

  1. stirringthe resulting mixture was stirred for 30 min
  2. extractionThe mixture was extracted with ethylacetate (3×20 ml)
  3. customCollected organics after solvent evaporation

Sources & evidence

ORD record
ord-a74b8cbbab8e45ecb1597c2d25e7c5e3
Source dataset
uspto-grants-2014_09
Patent number
US08828987B2

Reaction notes

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