Sodium Bicarbonate → 3,5-Dichlorobenzyl 3-((tert-butoxycarbonyl)amino)pyrrolidine-1-carboxylate

HRID 1480457Notes

Reaction equation

HRID 1480457 reaction equation
[C:1]([NH:8][CH:9]1[CH2:13][CH2:12][NH:11][CH2:10]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(=O)(O)[O-].[Na+].[C:19](Cl)(=[O:30])[O:20][CH2:21][C:22]1[CH:27]=[C:26]([Cl:28])[CH:25]=[C:24]([Cl:29])[CH:23]=1>C(Cl)Cl>[C:4]([O:3][C:1]([NH:8][CH:9]1[CH2:13][CH2:12][N:11]([C:19]([O:20][CH2:21][C:22]2[CH:23]=[C:24]([Cl:29])[CH:25]=[C:26]([Cl:28])[CH:27]=2)=[O:30])[CH2:10]1)=[O:2])([CH3:7])([CH3:6])[CH3:5]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 2757234tert-butyl N-(pyrrolidin-3-yl)carbamateHCID 133055323,5-Dichlorobenzyl Chloroformate

Product 1

HCID 867226833,5-Dichlorobenzyl 3-((tert-butoxycarbonyl)amino)pyrrolidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture comprising of 3-(boc-amino)pyrrolidine (1 g, 5.37 mmol) and saturated sodium bicarbonate (9 mL, 5.37 mmol) in DCM (17.90 mL) was stirred at room temperature for 5 minutes. The resulting mixture was treated with 3,5-dichlorobenzyl carbonochloridate (1.286 g, 5.37 mmol) and stirred at room temperature for one hour. The reaction mixture was concentrated under reduced pressure, diluted with water and extracted with DCM. The organic portion was separated and dried over MgSO4, filtered and concentrated under reduced pressure to afford the title compound;

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additiondiluted with water
  3. extractionextracted with DCM
  4. customThe organic portion was separated
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-02d8b1e9b91241409722871634c552dc
Source dataset
uspto-grants-2016_08
Patent number
US09409895B2

Reaction notes

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