Pyridine → HCID 58010302, compound

HRID 1854316Notes

Reaction equation

HRID 1854316 reaction equation
[NH:1]1[CH2:5][CH2:4][C@@H:3]([NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10])[CH2:2]1.N1C=CC=CC=1.[Cl:20][C:21](Cl)([O:23]C(=O)OC(Cl)(Cl)Cl)Cl>C(Cl)Cl>[Cl:20][C:21]([N:1]1[CH2:5][CH2:4][C@@H:3]([NH:6][C:7](=[O:13])[O:8][C:9]([CH3:10])([CH3:12])[CH3:11])[CH2:2]1)=[O:23]

Participants

5

Reactant 3

HCID 1049PyridineHCID 94429TriphosgeneHCID 1514397(3R)-(+)-3-(tert-Butoxycarbonylamino)pyrrolidine

Product 1

HCID 58010302HCID 58010302, compoundYield 248.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A flask was charged with (R)-tert-butyl pyrrolidin-3-ylcarbamate (1.0 g, 5.4 mmol, Lancaster) in DCM (15 mL) to give a colorless solution. Pyridine (0.89 mL, 10.8 mmol) was added and the solution was cooled to about 0° C., followed by the addition of triphosgene (0.64 g, 2.1 mmol). The mixture was stirred for about 1 h while slowly warming to ambient temperature. To the reaction solution was added DCM (50 mL) and the solution was washed with water (20 mL) and HCl (1N, 10 mL). The organic portion was separated, dried over anhydrous MgSO4, filtered, and concentrated to dryness under reduced pressure to give (R)-tert-butyl 1-(chlorocarbonyl)pyrrolidin-3-ylcarbamate (1.3 g, 98%) as a yellow oil: 1H NMR (DMSO-d6) δ 7.28 (s, 1 H), 4.03 (m, 1 H), 3.73-3.20 (m, 4 H), 2.05 (m, 1 H), 1.81 (m, 1 H), 1.39 (s, 9 H).

Workup

  1. customto give a colorless solution
  2. temperaturewhile slowly warming to ambient temperature
  3. washthe solution was washed with water (20 mL) and HCl (1N, 10 mL)
  4. customThe organic portion was separated
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-fc259dae33b4424dae3f031f5580c948
Source dataset
uspto-grants-2015_02
Patent number
US08962629B2

Reaction notes

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