HCID 16093618, compound → methyl (S)-4-(2-pyrrolidinylmethoxy)benzoate

HRID 350348Notes

Reaction equation

HRID 350348 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13][O:14][C:15]1[CH:24]=[CH:23][C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:17][CH:16]=1)=O)(C)(C)C>C(O)(C(F)(F)F)=O.C(Cl)Cl>[NH:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13][O:14][C:15]1[CH:24]=[CH:23][C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:17][CH:16]=1

Participants

4

Reactant 1

HCID 16093618HCID 16093618, compound

Product 1

HCID 16093581methyl (S)-4-(2-pyrrolidinylmethoxy)benzoateYield 73%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A mixture of methyl (S)-4-[1-(tert-butoxycarbonyl)-2-pyrrolidinylmethoxy]benzoate (3.34 g, 9.96 mmol) in TFA (20 mL) and CH2Cl2 (35 mL) was stirred at room temp for 15 hr. The mixture was concentrated in vacuo and made basic with sat. NaHCO3. The mixture was extracted with CHCl3, washed with brine, and dried over Na2CO3. The organic layer was evaporated to give 1.70 g (73%) methyl (S)-4-(2-pyrrolidinylmethoxy)benzoate as a yellow oil. 1H-NMR (CDCl3) δ 1.54–1.61 (m, 1 H), 1.77–1.86 (m, 2 H), 1.87–1.97 (m, 1 H), 2.00 (bs, 1 H), 2.93–3.06 (m, 2 H), 3.52–3.57 (m, 1 H), 3.88 (s, 3 H), 3.90–3.99 (m, 2 H), 6.92 (d, J=9.0 Hz, 2 H), 7.98 (d, J=9.0 Hz, 2 H)

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. extractionThe mixture was extracted with CHCl3
  3. washwashed with brine
  4. dry with materialdried over Na2CO3
  5. customThe organic layer was evaporated

Sources & evidence

ORD record
ord-fa386f74070c480c9c08f091795a65ec
Source dataset
uspto-grants-2007_02
Patent number
US07179819B2

Reaction notes

Loading…