Lithium hydroxide, monohydrate → [4-(2,3-Dihydro-benzofuran-5-carbonyl)-piperidin-1-yl]-acetic acid

HRID 713453Notes

Reaction equation

HRID 713453 reaction equation
C([O:3][C:4](=[O:23])[CH2:5][N:6]1[CH2:11][CH2:10][CH:9]([C:12]([C:14]2[CH:15]=[CH:16][C:17]3[O:21][CH2:20][CH2:19][C:18]=3[CH:22]=2)=[O:13])[CH2:8][CH2:7]1)C.O[Li].O>>[O:21]1[C:17]2[CH:16]=[CH:15][C:14]([C:12]([CH:9]3[CH2:8][CH2:7][N:6]([CH2:5][C:4]([OH:23])=[O:3])[CH2:11][CH2:10]3)=[O:13])=[CH:22][C:18]=2[CH2:19][CH2:20]1

Participants

3

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 71227106[4-(2,3-Dihydro-benzofuran-5-carbonyl)-piperidin-1-yl]-acetic acid ethyl ester

Product 1

HCID 71227107[4-(2,3-Dihydro-benzofuran-5-carbonyl)-piperidin-1-yl]-acetic acidYield 93%

Procedure

To a solution of [4-(2,3-dihydro-benzofuran-5-carbonyl)-piperidin-1-yl]-acetic acid ethyl ester (0.18 g, 0.57 mmol in 6 mL of THF and 2 mL of methanol) was added LiOH.H2O (0.12 g, 2.8 mmol in 3 mL of water) and the reaction mixture was stirred at ambient temperature for 1.5 hours. The solvent was removed in vacuo then diluted with 20 mL of water (pH 14). The residue was treated with 12 mL of 1 N HCl (pH 4), frozen at −78° C. and lyophilized for 24 hours to yield the title compound (0.16 g, 0.53 mmol). MS (ESI) m/z 289.7 (M+H+); HPLC (Novapak 150×3.9 mm C-18 column: mobile phase: 35-90% acetonitrile/water with 0.1% TFA, at 2 mL/min over 2 min.) t 1.23 min.

Workup

  1. customThe solvent was removed in vacuo
  2. additionthen diluted with 20 mL of water (pH 14)
  3. additionThe residue was treated with 12 mL of 1 N HCl (pH 4)
  4. temperaturefrozen at −78° C.
  5. waitlyophilized for 24 hours

Sources & evidence

ORD record
ord-760afa98d2944d26b7da20d87625350c
Source dataset
uspto-grants-2015_11
Patent number
US09181266B2

Reaction notes

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