Water → (R)-(+)-1-Boc-3-aminopyrrolidine

HRID 1813992Notes

Reaction equation

HRID 1813992 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@@H:10]([NH:13]C(=O)C(F)(F)F)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O.O.[OH-].[Li+]>C1COCC1>[NH2:13][C@@H:10]1[CH2:11][CH2:12][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:9]1

Participants

5

Reactant 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrate2×HCID 86588261HCID 86588261, compound

Product 1

HCID 854070(R)-(+)-1-Boc-3-aminopyrrolidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

tert-Butyl-(3R)-3-[(trifluoroacetyl)amino]pyrrolidine-1-carboxylate 6-1 (6.30 g, 22.32 mmol) was dissolved in 80 mL of 4:1 THF: H2O. Lithium hydroxide hydrate (1.873 g, 44.64 mmol) was added and the reaction was stirred at room temperature. After 24 hours more lithium hydroxide hydrate (2.810 g, 66.96 mmol) was added. After 30 hours the solution was concentrated in vacuo (to remove THE) then extracted with EtOAc (3×). The combined organic layers were dried (Na2SO4), filtered, and concentrated to afford tert-butyl (3R)-3-aminopyrrolidine-1-carboxylate 6-2 as a yellow oil. Free base: 1H NMR (DMSO-d6) δ 3.45-3.14 (m, 4H), 2.88-2.83 (m, 1H), 1.92-1.77 (m, 1H), 1.61 (s, 2H), 1.56-1.46 (m, 1H), 1.39 (s, 9H).

Workup

  1. concentrationAfter 30 hours the solution was concentrated in vacuo (
  2. customto remove THE)
  3. extractionthen extracted with EtOAc (3×)
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e2029d76a5484001b6c9dc8b2565d25e
Source dataset
uspto-grants-2005_04
Patent number
US06875767B2

Reaction notes

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