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

HRID 73036Notes

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-c4823322e0294ff6afe5fe0a86abe42a
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08828996B2

Reaction notes

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