1-Isocyanatoadamantane → (+/-)-Ethyl 2-(7-bromo-1'-((1-adamantyl)carbamoyl)-2,3-dihydrospiro[indene-1,4'-piperidine]-3-yl)acetate

HRID 1424609Notes

Reaction equation

HRID 1424609 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:15]=1[C:9]1([CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1)[CH2:8][CH:7]2[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18].[C:22]12([N:32]=[C:33]=[O:34])[CH2:31][CH:26]3[CH2:27][CH:28]([CH2:30][CH:24]([CH2:25]3)[CH2:23]1)[CH2:29]2>>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:15]=1[C:9]1([CH2:10][CH2:11][N:12]([C:33](=[O:34])[NH:32][C:22]34[CH2:23][CH:24]5[CH2:30][CH:28]([CH2:27][CH:26]([CH2:25]5)[CH2:31]3)[CH2:29]4)[CH2:13][CH2:14]1)[CH2:8][CH:7]2[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18]

Participants

3

Reactant 2

HCID 20599951-IsocyanatoadamantaneHCID 58137336Ethyl 2-(7-bromo-2,3-dihydrospiro[indene-1,4'-piperidine]-3-yl)acetate

Product 1

HCID 86650839(+/-)-Ethyl 2-(7-bromo-1'-((1-adamantyl)carbamoyl)-2,3-dihydrospiro[indene-1,4'-piperidine]-3-yl)acetate

Procedure

The title compound was prepared from (±)-ethyl 2-(7-bromo-2,3-dihydrospiro[indene-1,4′-piperidine]-3-yl)acetate and 1-adamantyl isocyanate following a procedure analogous to that described in Example 57. LC-MS Method 1 tR=2.32 min, m/z=531; 1H NMR (CDCl3) δ=7.38 (d, 1H), 7.12-7.04 (m, 2H), 4.19 (q, 2H), 3.87 (m, 2H), 3.57 (m, 1H), 3.13-2.83 (m, 4H), 2.63 (dd, 1H), 2.44 (m, 2H), 1.42 (d, 2H), 1.29 (t, 3H).

Sources & evidence

ORD record
ord-e9027b2a65d34909a30c36a2bbd15bd3
Source dataset
uspto-grants-2015_01
Patent number
US08927715B2

Reaction notes

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