Lithium Hydroxide → HCID 66953425, compound

HRID 1424631Notes

Reaction equation

HRID 1424631 reaction equation
C([O:3][C:4]([CH:6]1[CH2:8][CH:7]1[C:9]([N:11]1[CH2:38][C:19]2([CH2:24][CH2:23][N:22]([C:25]([O:27][CH:28]3[CH:35]4[CH2:36][CH:31]5[CH2:32][CH:33]([CH2:37][CH:29]3[CH2:30]5)[CH2:34]4)=[O:26])[CH2:21][CH2:20]2)[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:12]1)=[O:10])=[O:5])C.[Li+].[OH-]>C(#N)C>[CH:29]12[CH2:37][CH:33]3[CH2:32][CH:31]([CH2:36][CH:35]([CH2:34]3)[CH:28]1[O:27][C:25]([N:22]1[CH2:21][CH2:20][C:19]3([C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[CH2:12][N:11]([C:9]([CH:7]4[CH2:8][CH:6]4[C:4]([OH:5])=[O:3])=[O:10])[CH2:38]3)[CH2:24][CH2:23]1)=[O:26])[CH2:30]2

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 76657509HCID 76657509, compound

Product 1

HCID 66953425HCID 66953425, compoundYield 54.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-Adamantyl 2-((1RS,2RS)-2-(ethoxycarbonyl)cyclopropanecarbonyl)-2,3-dihydro-1H-spiro[isoquinoline-4,4′-piperidine]-1′-carboxylate (9 mg, 0.017 mmol) was mixed with 2N aq LiOH (2004, excess) and acetonitrile (3 mL). The mixture was stirred overnight at rt. LC-MS showed the reaction was complete. The mixture was concentrated, acidified with 5% aq HCl and extracted with EtOAc (3×3 mL). The combined organic layers were concentrated and purified by preparative HPLC to afford (1RS,2RS)-2-(1′-(2-adamantyloxycarbonyl)-2,3-dihydro-1H-spiro[isoquino line-4,4′-piperidine]-2-ylcarbonyl)cyclopropanecarboxylic acid (4.6 mg, 54%). LC-MS Method 1 tR=1.98 min, m/z=493; 1H NMR (CDCl3) δ=7.37 (t, 1H), 7.31-7.19 (m, 2H), 7.13 (d, 1H), 4.89 (m, 3H), 4.16 (m, 3H), 3.15 (m, 2H), 2.50 (m, 1H), 2.29 (m, 1H).

Workup

  1. concentrationThe mixture was concentrated
  2. extractionextracted with EtOAc (3×3 mL)
  3. concentrationThe combined organic layers were concentrated
  4. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-e4db460b6d0e4a3aa52fc9288c040802
Source dataset
uspto-grants-2015_01
Patent number
US08927715B2

Reaction notes

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