Lithium Hydroxide → HCID 25065227, compound

HRID 1424607Notes

Reaction equation

HRID 1424607 reaction equation
[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH:2]1[NH:11][C:12]([N:14]1[CH2:19][CH2:18][C:17]3([C:27]4[C:22](=[CH:23][CH:24]=[C:25]([Cl:28])[CH:26]=4)[CH:21]([CH2:29][C:30]([O:32]CC)=[O:31])[CH2:20]3)[CH2:16][CH2:15]1)=[O:13])[CH2:8]2.[Li+].[OH-]>CO>[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH:2]1[NH:11][C:12]([N:14]1[CH2:19][CH2:18][C:17]3([C:27]4[C:22](=[CH:23][CH:24]=[C:25]([Cl:28])[CH:26]=4)[CH:21]([CH2:29][C:30]([OH:32])=[O:31])[CH2:20]3)[CH2:16][CH2:15]1)=[O:13])[CH2:8]2

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 25065228HCID 25065228, compound

Product 1

HCID 25065227HCID 25065227, compoundYield 7.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (±)-ethyl 2-(1′-((2-adamantyl)carbamoyl)-6-chloro-2,3-dihydrospiro[indene-1,4′-piperidine]-3-yl)acetate (150 mg, 0.3 mmol) in MeOH (3 mL), LiOH (15 mg, 0.6 mmol) was added and the mixture was stirred for 2 h. The solution was concentrated to give the residue, which was purified by preparative HPLC to obtain (±)-2-(1′-((2-adamantyl)carbamoyl)-6-chloro-2,3-dihydrospiro[indene-1,4′-piperidine]-3-yl)acetic acid (10 mg, 7%). LC-MS Method 5 tR=1.485 min, m/z=457.2; 1H NMR (CD3OD): δ=1.59-1.76 (m, 6H), 1.86-1.99 (m, 8H), 1.99-2.19 (m, 6H), 2.48-2.57 (m, 1H), 2.78 (m, 1H), 2.95 (m, 1H), 3.00-3.09 (m, 1H), 3.11-3.23 (m, 1H), 3.69 (m, 1H), 3.94 (s, 1H), 4.06-4.19 (m, 2H), 7.26 (m, 3H).

Workup

  1. concentrationThe solution was concentrated
  2. customto give the residue, which
  3. customwas purified by preparative HPLC

Sources & evidence

ORD record
ord-95164c8a56234fa7b306bb5b46c1a3db
Source dataset
uspto-grants-2015_01
Patent number
US08927715B2

Reaction notes

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