Dichloromethane → Phenylmethyl tetrahydro-1H-furo[3,4-c]pyrrole-5(3H)-carboxylate

HRID 1366460Notes

Reaction equation

HRID 1366460 reaction equation
C(Cl)Cl.O[CH2:5][C@H:6]1[C@@H:10]([CH2:11][OH:12])[CH2:9][N:8]([C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:14])[CH2:7]1.S(Cl)(C1C=CC(C)=CC=1)(=O)=O>N1C=CC=CC=1>[CH2:11]1[CH:10]2[CH2:9][N:8]([C:13]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[O:14])[CH2:7][CH:6]2[CH2:5][O:12]1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 73974-Toluenesulfonyl chlorideHCID 66936428benzyl (3R,4S)-3,4-bis(hydroxymethyl)pyrrolidine-1-carboxylate

Product 1

HCID 66936078Phenylmethyl tetrahydro-1H-furo[3,4-c]pyrrole-5(3H)-carboxylate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a mixture of DCM (3 mL) and pyridine (3 mL) was added phenylmethyl (cis)-3,4-bis(hydroxymethyl)-1-pyrrolidinecarboxylate (250 mg, 0.94 mmol) followed by tosyl-chloride (540 mg, 2.8 mmol) and the resulting solution was refluxed for 4 hours. The solvents were evaporated and the residue was azeotroped once with hexane before being purified by RP-HPLC. This yielded phenylmethyl tetrahydro-1H-furo[3,4-c]pyrrole-5(3H)-carboxylate (170 mg, 73%). LCMS: (M+H)+: 248.4.

Workup

  1. temperaturethe resulting solution was refluxed for 4 hours
  2. customThe solvents were evaporated
  3. customthe residue was azeotroped once with hexane
  4. custombefore being purified by RP-HPLC

Sources & evidence

ORD record
ord-708633cb22204ee2b859db60cd2f560d
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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