Trifluoroacetic acid → Benzyl N-[(3R,4R)-4-hydroxypyrrolidin-3-YL]carbamate

HRID 338961Notes

Reaction equation

HRID 338961 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]1[C@H:16]([OH:17])[CH2:15][N:14](C(OC(C)(C)C)=O)[CH2:13]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[OH:17][C@@H:16]1[CH2:15][NH:14][CH2:13][C@H:12]1[NH:11][C:9](=[O:10])[O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57970124trans-Tert-butyl 3-(((benzyloxy)carbonyl)amino)-4-hydroxypyrrolidine-1-carboxylate

Product 1

HCID 68219095Benzyl N-[(3R,4R)-4-hydroxypyrrolidin-3-YL]carbamateYield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (3R,4R)-tert-butyl 3-(benzyloxycarbonylamino)-4-hydroxypyrrolidine-1-carboxylate (4.91 g, 14.60 mmol) in DCM (20 mL) was added TFA (11.25 mL, 146.0 mmol) and the mixture was stirred at ambient temperature for 1 hour. The solvent was removed under reduced pressure. 6 N HCl in water (10 mL) was added. The mixture was stirred at ambient temperature for 30 minutes and neutralized with saturated sodium bicarbonate to about pH 8. It was extracted with DCM:IPA=4:1 (50 mL). The organic layer was separated, dried (sodium sulfate), filtered and concentrated under reduced pressure to give benzyl (3R,4R)-4-hydroxypyrrolidin-3-ylcarbamate (2.45 g, 71.0%) as a solid.

Workup

  1. customThe solvent was removed under reduced pressure
  2. addition6 N HCl in water (10 mL) was added
  3. stirringThe mixture was stirred at ambient temperature for 30 minutes
  4. extractionIt was extracted with DCM
  5. customThe organic layer was separated
  6. dry with materialdried (sodium sulfate)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-fe7a72db9372468bb8044420d59b58d4
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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