Carbon Dioxide → tert-Butyl 3-(hydroxymethyl)pyrrolidine-1-carboxylate

HRID 401800Notes

Reaction equation

HRID 401800 reaction equation
[NH:1]1[CH2:5][CH2:4][CH:3]([CH2:6][OH:7])[CH2:2]1.[C:8](=O)([O:14]C(C)(C)C)[O:9][C:10]([CH3:13])([CH3:12])[CH3:11].C(=O)=O>C1COCC1>[OH:7][CH2:6][CH:3]1[CH2:4][CH2:5][N:1]([C:8]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:14])[CH2:2]1

Participants

5

Reactant 3

HCID 280Carbon DioxideHCID 10219638Carbonic acid, bis(1,1-dimethylethyl) esterHCID 13400657(Pyrrolidin-3-yl)methanol

Product 1

HCID 5237175tert-Butyl 3-(hydroxymethyl)pyrrolidine-1-carboxylateYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a boiled solution of pyrrolidin-3-ylmethanol (Preparation 64, 52.4 g, 0.518 mol, 1 eq) in THF (200 mL) was added dropwise under stirring a solution of di-tert-butyl carbonate (114.2 g, 0.523 mol, 1.01 eq) in THF (100-10 mL) during 1.5 h. After carbon dioxide evolution ceased, the mixture was refluxed for 2.5-3 h and cooled to give a yellowish solution. Solvents were removed on a rotary evaporator from this solution. Yellowish viscous oily residue was vacuum-dried to constant weight to give title compound (104 g, 0.518 mol, 100%).

Workup

  1. temperaturethe mixture was refluxed for 2.5-3 h
  2. temperaturecooled
  3. customto give a yellowish solution
  4. customSolvents were removed on a rotary evaporator from this solution
  5. customYellowish viscous oily residue was vacuum-dried to constant weight

Sources & evidence

ORD record
ord-ba221616456d4539bbd7b55b0d4af7e8
Source dataset
uspto-grants-2014_06
Patent number
US08741934B2

Reaction notes

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