Trifluoroacetic acid → (3R)-1-(Oxetan-3-yl)pyrrolidin-3-amine

HRID 1043250Notes

Reaction equation

HRID 1043250 reaction equation
[O:1]1[CH2:4][CH:3]([N:5]2[CH2:9][CH2:8][C@@H:7]([NH:10]C(=O)OC(C)(C)C)[CH2:6]2)[CH2:2]1.FC(F)(F)C(O)=O>ClCCl>[O:1]1[CH2:4][CH:3]([N:5]2[CH2:9][CH2:8][C@@H:7]([NH2:10])[CH2:6]2)[CH2:2]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 56604507(R)-tert-butyl 1-(oxetan-3-yl)pyrrolidin-3-ylcarbamate

Product 1

HCID 56604369(3R)-1-(Oxetan-3-yl)pyrrolidin-3-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of EXAMPLE 455A (0.7 g) in dichloromethane (2 mL) was added trifluoroacetic acid (2.2 mL). The reaction was stirred for 4 hours and concentrated. The concentrate was loaded onto an ion exchange column (Bond Elut Plexa column from Varian) which had been previously washed with 1:1 methanol/CH2Cl2. The trifluoroacetic acid was washed through with 1:1 methanol/CH2Cl2. The column was then eluted with 7 N NH3 in methanol to give the title compound.

Workup

  1. concentrationconcentrated
  2. washhad been previously washed with 1:1 methanol/CH2Cl2
  3. washThe trifluoroacetic acid was washed through with 1:1 methanol/CH2Cl2
  4. washThe column was then eluted with 7 N NH3 in methanol

Sources & evidence

ORD record
ord-43d17e6b8eff452cb2a3ea1f9b6161c2
Source dataset
uspto-grants-2013_10
Patent number
US08557983B2

Reaction notes

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