Methylparaben → HCID 16093618, compound

HRID 350347Notes

Reaction equation

HRID 350347 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.[C:12]([N:19]1[CH2:25][CH2:24][CH2:23][C@H:20]1[CH2:21]O)([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[C:15]([O:14][C:12]([N:19]1[CH2:25][CH2:24][CH2:23][C@H:20]1[CH2:21][O:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:10][CH:11]=1)=[O:13])([CH3:18])([CH3:16])[CH3:17]

Participants

6

Reactant 4

HCID 7456MethylparabenHCID 11776TriphenylphosphineHCID 643448(S)-(-)-N-Boc-prolinolHCID 5363146Diisopropyl azodicarboxylate

Product 1

HCID 16093618HCID 16093618, compoundYield 77.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of methyl 4-hydroxybenzoate (1.96 g, 12.88 mmol), N-Boc-prolinol (2.59 g, 12.87 mmol) and PPh3 (4.06 g, 15.48 mmol) in THF (40 mL) was added DIAD (3.10 mL, 15.74 mmol). The resulting mixture was heated under reflux for 14 hr. The mixture was evaporated off in vacuo and the residue was purified by column chromatography on silica-gel with n-hexane-EtOAc (6:1, v/v) as eluent to give 3.34 g (77%) methyl (S)-4-[1-(tert-butoxycarbonyl)-2-pyrrolidinylmethoxy]benzoate as an oil. 1H-NMR (CDCl3) δ 1.48 (s, 9 H), 1.67 (d, J=9.3 Hz, 1 H), 1.87–2.03 (m, 3 H), 3.36–3.43 (m, 2H), 3.874.09 (m,l1H), 4.13–4.20 (m, 2 H, 6.94 (d, J=8.3 Hz, 2H), 7.98 (d, J=8.3 Hz, 2H).

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureunder reflux for 14 hr
  3. customThe mixture was evaporated off in vacuo
  4. customthe residue was purified by column chromatography on silica-gel with n-hexane-EtOAc (6:1

Sources & evidence

ORD record
ord-b36b33e3d8934e049fd423f3423cca7b
Source dataset
uspto-grants-2007_02
Patent number
US07179819B2

Reaction notes

Loading…