Lithium hydroxide, monohydrate → HCID 71226956, compound

HRID 713463Notes

Reaction equation

HRID 713463 reaction equation
C([O:3][C:4](=[O:24])[CH2:5][N:6]1[CH2:11][CH2:10][CH:9]([C:12](=[O:23])[C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH3:21])=[C:15]([F:22])[CH:14]=2)[CH2:8][CH2:7]1)C.O[Li].O>>[CH2:20]([O:19][C:16]1[CH:17]=[CH:18][C:13]([C:12]([CH:9]2[CH2:10][CH2:11][N:6]([CH2:5][C:4]([OH:24])=[O:3])[CH2:7][CH2:8]2)=[O:23])=[CH:14][C:15]=1[F:22])[CH3:21]

Participants

3

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 71227170HCID 71227170, compound

Product 1

HCID 71226956HCID 71226956, compoundYield 98.2%

Procedure

To a solution of [4-(4-ethoxy-3-fluoro-benzoyl)-piperidin-1-yl]-acetic acid ethyl ester (0.19 g, 0.56 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 (0.17 g, 0.55 mmol,). MS (ESI) m/z 310.4 (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 1.86 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-0c82e58e410845d38cf1f52efe9ac980
Source dataset
uspto-grants-2015_11
Patent number
US09181266B2

Reaction notes

Loading…