Ammonium formate → [10-(2-Hydroxyethyl)-11-oxa-3,8-diazaspiro[5.5]undecan-3-yl]-(4-isopropoxy-3-methyl-phenyl)methanone hydrochloride salt

HRID 713122Notes

Reaction equation

[ClH:1].C([N:9]1[CH2:32][CH:31]([CH2:33][CH2:34][OH:35])[O:30][C:11]2([CH2:16][CH2:15][N:14]([C:17]([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH:26]([CH3:28])[CH3:27])=[C:21]([CH3:29])[CH:20]=3)=[O:18])[CH2:13][CH2:12]2)[CH2:10]1)C1C=CC=CC=1.C([O-])=O.[NH4+]>CO.[Pd]>[ClH:1].[OH:35][CH2:34][CH2:33][CH:31]1[O:30][C:11]2([CH2:16][CH2:15][N:14]([C:17]([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH:26]([CH3:28])[CH3:27])=[C:21]([CH3:29])[CH:20]=3)=[O:18])[CH2:13][CH2:12]2)[CH2:10][NH:9][CH2:32]1

Participants

Conditions

Temperature: 75 °C

Procedure

To a solution of [8-benzyl-10-(2-hydroxyethyl)-11-oxa-3,8-diazaspiro[5.5]undecan-3-yl]-(4-isopropoxy-3-methyl-phenyl)methanone hydrochloride salt (40 mg, 0.08 mmol) in methanol (750 μL) was added Pd (4 mg, 0.004 mmol) and ammonium formate (25 mg, 0.39 mmol), and the reaction mixture was heated at 75° C. for 1 hour. The reaction mixture was microfiltered and purified by prep LCMS (1-99% ACN/Water, 5 mM HCl modifier) to give [10-(2-hydroxyethyl)-11-oxa-3,8-diazaspiro[5.5]undecan-3-yl]-(4-isopropoxy-3-methyl-phenyl)methanone hydrochloride salt (20 mg, 62%). ESI-MS m/z calc. 376.2. found 377.3 (M+1)+; Retention time: 1.01 minutes (3 min run).

Workup

custompurified by prep LCMS (1-99% ACN/Water, 5 mM HCl modifier)

Sources & evidence

ORD record: ord-20538bdc764945efba216cd6c40c52d8
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181273B2

Reaction notes

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