Methylamine → HCID 25064189, compound

HRID 1424594Notes

Reaction equation

HRID 1424594 reaction equation
C[O:2][C:3](=O)[CH2:4][CH:5]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:7]2([CH2:12][CH2:11][N:10]([C:13]([O:15][CH:16]3[CH:23]4[CH2:24][CH:19]5[CH2:20][CH:21]([CH2:25][CH:17]3[CH2:18]5)[CH2:22]4)=[O:14])[CH2:9][CH2:8]2)[CH2:6]1.[CH3:33][NH2:34]>>[CH3:33][NH:34][C:3](=[O:2])[CH2:4][CH:5]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:7]2([CH2:12][CH2:11][N:10]([C:13]([O:15][CH:16]3[CH:23]4[CH2:22][CH:21]5[CH2:20][CH:19]([CH2:18][CH:17]3[CH2:25]5)[CH2:24]4)=[O:14])[CH2:9][CH2:8]2)[CH2:6]1

Participants

3

Reactant 2

HCID 6329MethylamineHCID 25064187HCID 25064187, compound

Product 1

HCID 25064189HCID 25064189, compoundYield 37%

Procedure

(±)-2-Adamantyl 3-(2-methoxy-2-oxoethyl)-2,3-dihydrospiro[indene-1,4′-piperidine]-1′-carboxylate (33 mg, 0.075 mmol) was added to a solution of methylamine in alcohol (2 mL) at 0° C. The above mixture was heated under reflux overnight. LC-MS showed that the starting material was consumed completely. The mixture was evaporated to give a residue, which was purified by preparative HPLC to obtain (±)-2-adamantyl 3-(2-(methylamino)-2-oxoethyl)-2,3-dihydrospiro[indene-1,4′-piperidine]-1′-carboxylate (12 mg, 37%). 1H-NMR (400 MHz, CD3OD): 8=-1.52-1.67 (m, 6H), 1.84 (m, 6H), 1.93 (m, 2H), 2.07 (M, 5H), 2.28 (m, 1H), 2.56 (m, 1H), 2.77 (m, 4H), 3.12 (br, 2H), 3.62 (m, 1H), 4.19 (br, 2H), 7.18 (m, 4H).

Workup

  1. temperatureThe above mixture was heated
  2. temperatureunder reflux overnight
  3. customwas consumed completely
  4. customThe mixture was evaporated
  5. customto give a residue, which
  6. customwas purified by preparative HPLC

Sources & evidence

ORD record
ord-25521625c9fc4a7c93abd0261013fa20
Source dataset
uspto-grants-2015_01
Patent number
US08927715B2

Reaction notes

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