Lithium hydroxide, monohydrate → HCID 66953399, compound

HRID 1424615Notes

Reaction equation

HRID 1424615 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:28]=1[C:9]1([CH2:14][CH2:13][N:12]([C:15](=[O:27])[NH:16][CH:17]3[CH:24]4[CH2:25][CH:20]5[CH2:21][CH:22]([CH2:26][CH:18]3[CH2:19]5)[CH2:23]4)[CH2:11][CH2:10]1)[CH2:8][CH:7]2[CH:29]([CH3:35])[C:30]([O:32]CC)=[O:31].O[Li].O>CO.O>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:28]=1[C:9]1([CH2:10][CH2:11][N:12]([C:15](=[O:27])[NH:16][CH:17]3[CH:18]4[CH2:26][CH:22]5[CH2:21][CH:20]([CH2:25][CH:24]3[CH2:23]5)[CH2:19]4)[CH2:13][CH2:14]1)[CH2:8][CH:7]2[CH:29]([CH3:35])[C:30]([OH:32])=[O:31]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 70795046HCID 70795046, compound

Product 1

HCID 66953399HCID 66953399, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution (±)-ethyl 2-(7-bromo-1′-(2-adamantylcarbamoyl)-2,3-dihydrospiro[indene-1,4′-piperidine]-3-yl)propanoate (63 mg, 0.122 mmol) in anhydrous MeOH (1 mL) was added LiOH.H2O (10 mg, 0.244 mmol) in H2O (0.1 mL). The reaction mixture was stirred at rt overnight. The mixture was concentrated to give crude product, which was purified by preparative TLC to afford 2-(7-bromo-1′-((2-adamantyl)carbamoyl)-2,3-dihydrospiro[indene-1,4′-piperidine]-3-yl)propanoic acid. 1H NMR: (400 MHz, CDCl3): δ=1.04 (s, 3H), 1.21 (s, 3H), 1.34-1.43 (m, 2H), 1.60-1.71 (m, 3H), 1.76-2.08 (m, 13H), 2.29-2.40 (m, 1H), 2.51-2.61 (m, 1H), 2.99-3.27 (m, 3H), 3.89 (m, 2H), 4.02-4.14 (m, 2H), 7.01 (m, 1H), 7.21-7.33 (m, 2H).

Workup

  1. concentrationThe mixture was concentrated
  2. customto give crude product, which
  3. customwas purified by preparative TLC

Sources & evidence

ORD record
ord-a9dfbe4868044b768cf7c738a1045beb
Source dataset
uspto-grants-2015_01
Patent number
US08927715B2

Reaction notes

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