Lithium hydroxide, monohydrate → HCID 25064188, compound

HRID 1424593Notes

Reaction equation

HRID 1424593 reaction equation
[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH:2]1[O:11][C:12]([N:14]1[CH2:19][CH2:18][C:17]3([C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[CH:21]([CH2:28][C:29]([O:31]C)=[O:30])[CH2:20]3)[CH2:16][CH2:15]1)=[O:13])[CH2:8]2.O[Li].O>CO.O>[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH:2]1[O:11][C:12]([N:14]1[CH2:15][CH2:16][C:17]3([C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[CH:21]([CH2:28][C:29]([OH:31])=[O:30])[CH2:20]3)[CH2:18][CH2:19]1)=[O:13])[CH2:8]2

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 25064187HCID 25064187, compound

Product 1

HCID 25064188HCID 25064188, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

2-adamantyl-3-(2-methoxy-2-oxoethyl)-2,3-dihydrospiro[indene-1,4′-piperidine]-1′-carboxylate (26 mg, 0.06 mmol) was dissolved in MeOH (1 mL) in an ice-water bath. A solution of LiOH.H2O (4.99 mg, 0.119 mmol) in water (0.2 mL) was added dropwise and the mixture was stirred for 8 h at rt. LC-MS showed that the starting material was consumed completely. The mixture was evaporated to give a residue, which was purified by preparative HPLC to afford 2-(1′-((2-adamantyloxy)carbonyl)-2,3-dihydrospiro[indene-1,4′-piperidine]-3-yl)acetic acid (12.2 mg, 48%). 1H NMR (400 MHz, CD3OD): δ=0.91 (m, 2H), 1.32 (m, 3H); 1.53-1.71 (m, 6H), 1.75-1.93 (m, 8H), 1.93-2.18 (m, 4H), 2.24 (m, 1H), 2.63 (m, 1H), 2.77 (m, 1H), 2.96-3.24 (br, 2H), 3.62 (m, 1H), 4.10-4.28 (br, 2H), 4.72 (s, 1H), 7.15 (m, 3H), 7.24 (m, 1H).

Workup

  1. customwas consumed completely
  2. customThe mixture was evaporated
  3. customto give a residue, which
  4. customwas purified by preparative HPLC

Sources & evidence

ORD record
ord-b8afe6ce6e614743bfbe6deb0d2baf7f
Source dataset
uspto-grants-2015_01
Patent number
US08927715B2

Reaction notes

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