Hydrochloric Acid → Benzyl 3-hydroxypyrrolidine-1-carboxylate

HRID 353958

Reaction equation

HRID 353958 reaction equation
[OH:1][CH:2]1[CH2:6][CH2:5][NH:4][CH2:3]1.[CH2:7]([O:14][C:15](Cl)=[O:16])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.Cl>[OH-].[Na+]>[CH2:7]([O:14][C:15]([N:4]1[CH2:5][CH2:6][CH:2]([OH:1])[CH2:3]1)=[O:16])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10387Benzyl chloroformateHCID 982104-Hydroxypyrrolidine

Product 1

HCID 560953Benzyl 3-hydroxypyrrolidine-1-carboxylateYield 95%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
0 °C

Procedure

3-Hydroxy-pyrrolidine (10 g, 115 mmol, 1.0 equiv) was dissolved in 2 N NaOH (100 mL) and the mixture was cooled to 0° C. Benzylchloroformate (21 g, 126 mmol, 1.1 equiv) was added dropwise over a 45 min period. After addition, the reaction was stirred at room temperature for 4 h at which time the pH was adjusted to 7-8 using concentrated HCl. The product was extracted with 3×100 mL of CH2Cl2. The organic extracts were combined and dried over Na2SO4, decanted and concentrated in vacuo to yield the desired product as a light yellow oil (24.1 g, 95%) that was used without further purification.

Workup

  1. additionAfter addition
  2. extractionThe product was extracted with 3×100 mL of CH2Cl2
  3. dry with materialdried over Na2SO4
  4. customdecanted
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-12dc2c2124274a21af420a798c4c5e0d
Source dataset
uspto-grants-2004_06
Patent number
US06756372B2

Linked notes

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