Trifluoroacetic acid → (+/-)-Phenylmethyl {[trans-4-hydroxy-3-pyrrolidinyl]methyl}carbamate

HRID 639086Notes

Reaction equation

HRID 639086 reaction equation
[OH:1][C@H:2]1[C@H:6]([CH2:7][NH:8][C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[CH2:5][N:4](C(OC(C)(C)C)=O)[CH2:3]1.C(O)(C(F)(F)F)=O.CC[NH+](CC)CC.CC[NH+](CC)CC.C([O-])([O-])=O>C(Cl)Cl>[OH:1][C@@H:2]1[CH2:3][NH:4][CH2:5][C@H:6]1[CH2:7][NH:8][C:9](=[O:10])[O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 15264167Carbonic acid--N,N-diethylethanamine (1/2)HCID 86616793(+/-)-1,1-Dimethylethyl trans-3-hydroxy-4-[({[(phenylmethyl)oxy]carbonyl}amino)methyl]-1-pyrrolidinecarboxylate

Product 1

HCID 86616792(+/-)-Phenylmethyl {[trans-4-hydroxy-3-pyrrolidinyl]methyl}carbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (±)-1,1-dimethylethyl trans-3-hydroxy-4-[({[(phenylmethyl)oxy]carbonyl}amino)methyl]-1-pyrrolidinecarboxylate (4.44 g, 12.7 mmole) in DCM (75 mL) was added TFA (25 mL). After stirring for 2 h, the reaction contents were concentrated under vacuum and the residue dissolved in DCM (150 mL). MP-carbonate resin (18.8 g, 50.8 mmole) was added and the reaction contents were stirred vigorously overnight. The reaction contents were filtered through a scinter-glass funnel and the resin washed with MeOH. The filtrate was concentrated and dried under vacuum to give an off-white foam: LC-MS (ES) m/e 251 (M+H)+.

Workup

  1. customthe reaction contents
  2. concentrationwere concentrated under vacuum
  3. dissolutionthe residue dissolved in DCM (150 mL)
  4. customthe reaction contents
  5. stirringwere stirred vigorously overnight
  6. customThe reaction contents
  7. filtrationwere filtered through a scinter-glass funnel
  8. washthe resin washed with MeOH
  9. concentrationThe filtrate was concentrated
  10. customdried under vacuum
  11. customto give an off-white foam

Sources & evidence

ORD record
ord-75ddd1ddd0434acf8a5833be87843a47
Source dataset
uspto-grants-2010_04
Patent number
US07691850B2

Reaction notes

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