Ammonium formate → Tert-butyl 10-(hydroxymethyl)-11-oxa-3,8-diazaspiro[5.5]undecane-3-carboxylate

HRID 712980Notes

Reaction equation

C([N:8]1[CH2:25][CH:24]([CH2:26][OH:27])[O:23][C:10]2([CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]2)[CH2:9]1)C1C=CC=CC=1.C([O-])=O.[NH4+]>[OH-].[OH-].[Pd+2]>[OH:27][CH2:26][CH:24]1[O:23][C:10]2([CH2:11][CH2:12][N:13]([C:16]([O:18][C:19]([CH3:21])([CH3:20])[CH3:22])=[O:17])[CH2:14][CH2:15]2)[CH2:9][NH:8][CH2:25]1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of tert-butyl 8-benzyl-10-(hydroxymethyl)-11-oxa-3,8-diazaspiro[5.5]undecane-3-carboxylate (4.10 g, 10.9 mmol), ammonium formate (6.87 g, 109 mmol) and Pd(OH)2 (1.53 g, 10.9 mmol) was heated at 60° C. for 1 h. The reaction mixture was cooled, filtered, and concentrated in vacuo to provide tert-butyl 10-(hydroxymethyl)-11-oxa-3,8-diazaspiro[5.5]undecane-3-carboxylate (3.10 g, 10.8 mmol, 99%). ESI-MS m/z calc. 286.2. found 287.2 (M+1)+; Retention time: 0.75 minutes (3 min run).

Workup

temperatureThe reaction mixture was cooled
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-9b5b20f82df34395af6132cca684f5de
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181273B2

Reaction notes

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