(3R)-1-[(tert-butoxy)carbonyl]pyrrolidine-3-carboxylic acid → tert-Butyl (3R)-3-(hydroxymethyl)pyrrolidine-1-carboxylate

HRID 2095433Notes

Reaction equation

HRID 2095433 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@@H:10]([C:13](O)=[O:14])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].B.C1COCC1>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@@H:10]([CH2:13][OH:14])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 1512491(3R)-1-[(tert-butoxy)carbonyl]pyrrolidine-3-carboxylic acidHCID 2723981Borane;tetrahydrofuran

Product 1

HCID 1514340tert-Butyl (3R)-3-(hydroxymethyl)pyrrolidine-1-carboxylateYield 96.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(tert-butoxycarbonyl)pyrrolidine-3(R)-carboxylic acid (800 mg, 3.72 mmol) in 20 mL of anhydrous THF was added dropwise BH3.THF complex (1M in THF, 7.4 mL, 2.0 equiv.) at 0° C. under N2. The resulting solution was stirred for 4 h at room temperature. The reaction was then quenched with water. The mixture was concentrated under vacuum and extracted with EtOAc. The combined organic layers were dried over Na2SO4 and concentrated in vacuo. The residue was applied onto a silica gel column, which was eluted with EtOAc/petroleum ether 1:5 to give the title compound (720 mg, 96%) as a colorless oil. LC-MS (ESI) m/z 202 (M+H+).

Workup

  1. customThe reaction was then quenched with water
  2. concentrationThe mixture was concentrated under vacuum
  3. extractionextracted with EtOAc
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. washwas eluted with EtOAc/petroleum ether 1:5

Sources & evidence

ORD record
ord-6e74723f2ac04014b93981397adb0969
Source dataset
uspto-grants-2013_05
Patent number
US08445684B2

Reaction notes

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