Ammonium Chloride → tert-butyl N-(2-hydroxy-3-pyrrolidinylpropoxy)carbamate

HRID 1978998Notes

Reaction equation

HRID 1978998 reaction equation
[O:1]1[CH2:13][CH:2]1[CH2:3][O:4][NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9].[NH:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1.[Cl-].[NH4+]>CO>[OH:1][CH:2]([CH2:13][N:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1)[CH2:3][O:4][NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 31268PyrrolidineHCID 18008120Tert-butyl (oxiran-2-ylmethoxy)carbamate

Product 1

HCID 56999457tert-butyl N-(2-hydroxy-3-pyrrolidinylpropoxy)carbamateYield 88%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 150 mg (0.79 mmol) portion of tert-butyl N-(2,3-epoxypropoxy)carbamate was dissolved in 1 ml of methanol, and the solution-was-mixed with 0.08 ml (0.95 mmol) of pyrrolidine and stirred at room temperature for 14 hours. The reaction solution was mixed with a saturated ammonium chloride aqueous solution and extracted with chloroform. The chloroform layer was washed with saturated brine and dried with anhydrous sodium sulfate, and then the solvent was evaporated under reduced pressure to obtain 181 mg (yield, 88%) of tert-butyl N-(2-hydroxy-3-pyrrolidinylpropoxy)carbamate.

Workup

  1. extractionextracted with chloroform
  2. washThe chloroform layer was washed with saturated brine
  3. dry with materialdried with anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-6f0b7338beda4bad95b7e61407843523
Source dataset
uspto-grants-2001_05
Patent number
US06239168B1

Reaction notes

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