Water → HCID 69840849, compound

HRID 1813993Notes

Reaction equation

HRID 1813993 reaction equation
[NH2:1][C@@H:2]1[CH2:6][CH2:5][N:4]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:3]1.[CH3:14][N:15]=[C:16]=[O:17].O>C(Cl)Cl>[CH3:14][NH:15][C:16]([NH:1][C@@H:2]1[CH2:6][CH2:5][N:4]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:3]1)=[O:17]

Participants

5

Reactant 3

HCID 962WaterHCID 12228Methyl IsocyanateHCID 854070(R)-(+)-1-Boc-3-aminopyrrolidine

Product 1

HCID 69840849HCID 69840849, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

tert-Butyl (3R)-3-aminopyrrolidine-1-carboxylate 6-2 (1.813 g, 9.73 mmol) was dissolved in 10 mL CH2Cl2. A solution of methylisocyanate (0.555 g, 9.73 mmol) in 10 mL CH2Cl2 was added. The solution was stirred for 3.5 hours. 50 mL H2O was added and the precipitate was extracted with CH2Cl2 (2×). The combined organic layers were dried (Na2SO4), filtered, and concentrated to afford tert-butyl (3R)-3-{[(methylamino)carbonyl]amino}pyrrolidine-1-carboxylate 6-3 as a white semi-solid. Free base: 1H NMR (DMSO-d6) δ 6.15 (bs, 1H), 5.63 (bd, 1H, J=4.22 Hz), 4.02 (m, 1H), 3.42-3.34 (m, 1H), 3.28-3.19 (m, 2H), 2.93-2.98 (m, 1H), 2.53 (d, 3H, J=4.58 Hz), 1.99-1.93 (m, 1H), 1.68-1.63 (m, 1H), 1.39 (s, 9H).

Workup

  1. extractionthe precipitate was extracted with CH2Cl2 (2×)
  2. dry with materialThe combined organic layers were dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-457b11efe29c429095eaa3c8be15f3cb
Source dataset
uspto-grants-2005_04
Patent number
US06875767B2

Reaction notes

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