Diisopropylethylamine → HCID 25065231, compound

HRID 1424608Notes

Reaction equation

HRID 1424608 reaction equation
[CH3:1][C:2]1[CH:15]=[C:14]2[C:5]([CH:6]([CH2:16][C:17]([OH:19])=[O:18])[CH2:7][C:8]32[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]3)=[CH:4][CH:3]=1.[CH:20]12[CH2:29][CH:24]3[CH2:25][CH:26]([CH2:28][CH:22]([CH2:23]3)[CH:21]1[N:30]=[C:31]=[O:32])[CH2:27]2.CCN(C(C)C)C(C)C>C(Cl)Cl.CCOC(C)=O>[CH:22]12[CH2:28][CH:26]3[CH2:25][CH:24]([CH2:29][CH:20]([CH2:27]3)[CH:21]1[NH:30][C:31]([N:11]1[CH2:10][CH2:9][C:8]3([C:14]4[C:5](=[CH:4][CH:3]=[C:2]([CH3:1])[CH:15]=4)[CH:6]([CH2:16][C:17]([OH:19])=[O:18])[CH2:7]3)[CH2:13][CH2:12]1)=[O:32])[CH2:23]2

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 128826302-IsocyanatoadamantaneHCID 58137291HCID 58137291, compound

Product 1

HCID 25065231HCID 25065231, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

(±)-2-(6-Methyl-2,3-dihydrospiro[indene-1,4′-piperidine]-3-yl)acetic acid (0.071 mmol), 2-adamantyl isocyanate (14 mg, 1 equiv) and i-Pr2NEt (37 μL, 3 equiv.) were dissolved in CH2Cl2 (3 mL) and put on a shaker for 1 h at rt. The mixture was diluted with EtOAc (10 mL), washed with 3% aq HCl (2×4 mL), concentrated and purified by preparative HPLC to afford (±)-2-(1′-((2-adamantyl)carbamoyl)-6-methyl-2,3-dihydrospiro[indene-1,4′-piperidine]-3-yl)acetic acid (20.4 mg, 66% yield). LC-MS Method 1 tR=1.93 min, m/z=437; 1H NMR (CDCl3) 7.05 (q, 2H), 6.96 (s, 1H), 4.94 (br s, 1H), 3.98 (s, 2H), 3.89 (d, 1H), 3.59 (m, 1H), 3.10-2.93 (m, 3H), 2.63 (dd, 1H), 2.43 (dd, 1H), 2.33 (s, 3H), 2.09 (td, 1H).

Workup

  1. washwashed with 3% aq HCl (2×4 mL)
  2. concentrationconcentrated
  3. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-0953ca36930a44fe80daaa7f29cc099c
Source dataset
uspto-grants-2015_01
Patent number
US08927715B2

Reaction notes

Loading…