Water → tert-butyl (2S)-2-cyanopyrrolidine-1-carboxylate

HRID 346464Notes

Reaction equation

HRID 346464 reaction equation
FC(F)(F)C(OC(=O)C(F)(F)F)=O.[C:14]([N:21]1[CH2:28][CH2:27][CH2:26][C@H:22]1[C:23]([NH-:25])=O)([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15].C(N(CC)CC)C.O>O1CCCC1>[C:14]([N:21]1[CH2:28][CH2:27][CH2:26][C@H:22]1[C:23]#[N:25])([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 178451937HCID 178451937, compound

Product 1

HCID 6951263tert-butyl (2S)-2-cyanopyrrolidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2.89 ml (20.8 mmol) trifluoroacetic acid anhydride was added to a solution of 4.05 g (18.9 mmol) BOC-L-prolyl-amide and 5.80 ml (41.6 mmol) triethyl amine in tetrahydrofuran at 0° C. The reaction was kept at rt for 2 h. 20 ml water was added, and the reaction was evaporated. The residue was dissolved in dichloromethane, and the organic phase was washed with 0.1 M HCl aq and 0.1 M NaOH aq. The organic phase was dried with anhydrous Na2SO4 and evaporated. Yield of crude product 3.64 g. The product was purified with a silica column using 25% ethyl acetate in petroleum ether as eluent. Yield 3.37 g (17.2 mmol, 91%).

Workup

  1. customthe reaction was evaporated
  2. dissolutionThe residue was dissolved in dichloromethane
  3. washthe organic phase was washed with 0.1 M HCl aq and 0.1 M NaOH aq. The organic phase
  4. dry with materialwas dried with anhydrous Na2SO4
  5. customevaporated
  6. customThe product was purified with a silica column

Sources & evidence

ORD record
ord-ddbb5517d5d84057a6b7671bdf6e5123
Source dataset
uspto-grants-2007_02
Patent number
US07173024B2

Reaction notes

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