Water → tert-Butyl 2-(hydroxymethyl)pyrrolidine-1-carboxylate

HRID 1283842Notes

Reaction equation

HRID 1283842 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:15][CH2:14][CH2:13][CH:9]1[C:10](O)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].B#B.O>O1CCCC1>[C:1]([O:5][C:6]([N:8]1[CH2:15][CH2:14][CH2:13][CH:9]1[CH2:10][OH:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 2684721-[(Tert-butoxy)carbonyl]pyrrolidine-2-carboxylic acidHCID 6328200Diboron

Product 1

HCID 550865tert-Butyl 2-(hydroxymethyl)pyrrolidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 21.6 g. (0.10 mol.) of N-t-butoxycarbonyl-DL-proline in 100 ml. of dry tetrahydrofuran at room temperature is added 50 ml. of a 1 molar diborane solution in tetrahydrofuran at such a rate that the temperature of the reaction mixture is maintained at 25°-30°. After the addition is complete, the reaction mixture is stirred at room temperature for an additional hour. Water is then cautiously added to the reaction mixture, the tetrahydrofuran is removed in vacuo, the residue is diluted with ether, and this solution is washed thoroughly with 5% aqueous sodium hydroxide. The ether solution is dried and concentrated in vacuo to obtain 1-(t-butoxycarbonyl)-2-pyrrolidinemethanol.

Workup

  1. additionAfter the addition
  2. customthe tetrahydrofuran is removed in vacuo
  3. additionthe residue is diluted with ether
  4. washthis solution is washed thoroughly with 5% aqueous sodium hydroxide
  5. dry with materialThe ether solution is dried
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-342edc5a3538406a8035fdefeed9076a
Source dataset
uspto-grants-1976_08
Patent number
US03976660

Reaction notes

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