2-Aminoadamantane → HCID 25065228, compound

HRID 1424606Notes

Reaction equation

HRID 1424606 reaction equation
[NH2:1][CH:2]1[CH:9]2[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:11][CH:3]1[CH2:4]3)[CH2:8]2.C1N=CN([C:17]([N:19]2[CH:23]=N[CH:21]=[CH:20]2)=[O:18])C=1.CCN(C(C)C)C(C)C.[Cl:33][C:34]1[CH:47]=[C:46]2[C:37]([CH:38]([CH2:48][C:49]([O:51][CH2:52][CH3:53])=[O:50])[CH2:39][C:40]32CCNC[CH2:41]3)=[CH:36][CH:35]=1>>[CH:9]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:11][CH:3]([CH2:4]3)[CH:2]1[NH:1][C:17]([N:19]1[CH2:20][CH2:21][C:40]3([C:46]4[C:37](=[CH:36][CH:35]=[C:34]([Cl:33])[CH:47]=4)[CH:38]([CH2:48][C:49]([O:51][CH2:52][CH3:53])=[O:50])[CH2:39]3)[CH2:41][CH2:23]1)=[O:18])[CH2:8]2

Participants

5

Reactant 4

HCID 253322-AminoadamantaneHCID 682631,1'-CarbonyldiimidazoleHCID 81531DiisopropylethylamineHCID 86650838HCID 86650838, compound

Product 1

HCID 25065228HCID 25065228, compoundYield 86%

Procedure

A solution of 2-aminoadamantane (123 mg, 0.66 mmol), CDI (107 mg, 0.66 mmol), DIEA (232 mg, 0.18 mmol) was stirred at 0° C. for 1 h. Then (±)-ethyl 2-(6-chloro-2,3-dihydrospiro[indene-1,4′-piperidine]-3-yl)acetate (180 mg, 0.60 mmol) was added to the solution and the mixture was stirred at rt overnight. The solvent was removed and the residue was purified by preparative TLC to give (±)-ethyl 2-(1′-((2-adamantyl)carbamoyl)-6-chloro-2,3-dihydrospiro[indene-1,4′-piperidine]-3-yl)acetate (250 mg, 86%). LC-MS Method 6 tR=1.492 min, m/z=485.2; 1H NMR (CDCl3): δ=1.29 (t, 3H), 1.56-1.66 (m, 4H), 1.66-1.80 (m, 6H), 1.85 (m, 5H), 1.93 (m, 2H), 2.04-2.16 (m, 1H), 2.37-2.49 (m, 1H), 2.56-2.65 (m, 1H), 2.88-2.92 (m, 1H), 3.00-3.20 (m, 2H), 3.55-3.66 (m, 1H), 3.81-3.90 (m, 1H), 3.90-4.00 (m, 2H), 4.20 (q, 2H), 5.26-5.50 (m, 3H), 7.07-7.14 (m, 2H), 7.19 (m, 1H).

Workup

  1. customThe solvent was removed
  2. customthe residue was purified by preparative TLC

Sources & evidence

ORD record
ord-af957370358b4e29b7eef1fe42c5e1a8
Source dataset
uspto-grants-2015_01
Patent number
US08927715B2

Reaction notes

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