(3R,4S)-tert-butyl 3-(benzyloxycarbonylamino)-4-(bis(4-methoxyphenyl)(phenyl)methoxy)pyrrolidine-1-carboxylate → Benzyl (3r,4s)-4-hydroxypyrrolidin-3-ylcarbamate

HRID 338942Notes

Reaction equation

HRID 338942 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]1[C@@H:16]([O:17]C(C2C=CC(OC)=CC=2)(C2C=CC(OC)=CC=2)C2C=CC=CC=2)[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.ClCCl>[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

3

Reactant 1

HCID 86707464(3R,4S)-tert-butyl 3-(benzyloxycarbonylamino)-4-(bis(4-methoxyphenyl)(phenyl)methoxy)pyrrolidine-1-carboxylate

Product 1

HCID 76849151Benzyl (3r,4s)-4-hydroxypyrrolidin-3-ylcarbamateYield 107.8%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

A solution of (3R,4S)-tert-butyl 3-(benzyloxycarbonylamino)-4-(bis(4-methoxyphenyl)(phenyl)methoxy)pyrrolidine-1-carboxylate (2.18 g, 3.14 mmol) was stirred in a 10% TFA/dichloromethane solution (30 mL) for 30 minutes. The solution was concentrated under reduced pressure and the residue dissolved in ethyl acetate (15 mL) and treated with 2N HCl-diethyl ether (30 mL) for 1 hour. The resulting precipitate was collected by filtration and washed with ethyl acetate and dried to an off-white solid. The solid was dissolved in a 50% MeOH:dichloromethane solution (30 mL) and stirred with solid sodium carbonate (5 g) for 2.5 hours. The solids were collected by filtration and washed with 50% MeOH/dichloromethane solution and the filtrate concentrated under reduced pressure to give benzyl (3R,4S)-4-hydroxypyrrolidin-3-ylcarbamate (0.80 g, 99%).

Workup

  1. concentrationThe solution was concentrated under reduced pressure
  2. dissolutionthe residue dissolved in ethyl acetate (15 mL)
  3. additiontreated with 2N HCl-diethyl ether (30 mL) for 1 hour
  4. filtrationThe resulting precipitate was collected by filtration
  5. washwashed with ethyl acetate
  6. customdried to an off-white solid
  7. dissolutionThe solid was dissolved in a 50% MeOH
  8. filtrationThe solids were collected by filtration
  9. washwashed with 50% MeOH/dichloromethane solution
  10. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-4c50108eeaa4499f877fb2a8da19e88a
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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