Diethyl Ether → HCID 71116334, compound

HRID 715515Notes

Reaction equation

HRID 715515 reaction equation
CS(O[CH2:6][C:7]1([CH2:27][O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH2:26][CH2:25][CH2:24][C:9]2([O:13][C:12](=[O:14])[N:11]([CH2:15][C:16]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=3)[CH2:10]2)[CH2:8]1)(=O)=O.[N-:36]=[N+:37]=[N-:38].[Na+].CCOCC>CS(C)=O.CCOC(C)=O>[N:36]([CH2:6][C:7]1([CH2:27][O:28][CH2:29][C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH2:26][CH2:25][CH2:24][C:9]2([O:13][C:12](=[O:14])[N:11]([CH2:15][C:16]3[CH:17]=[CH:18][C:19]([O:22][CH3:23])=[CH:20][CH:21]=3)[CH2:10]2)[CH2:8]1)=[N+:37]=[N-:38]

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 33557Sodium AzideHCID 86716582HCID 86716582, compound

Product 1

HCID 71116334HCID 71116334, compoundYield 93.9%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

To a light orange solution of (7-((benzyloxy)methyl)-3-(4-methoxybenzyl)-2-oxo-1-oxa-3-azaspiro[4.5]decan-7-yl)methyl methanesulfonate (5.71 g, 11.3 mmol) in DMSO (45.4 mL) was added sodium azide (2.21 g, 34.0 mmol). The reaction was heated at 120° C. behind a blast shield. After 4 days the reaction was cooled to RT and diluted with 1:1 EtOAc:Et2O (150 mL). This mixture was washed with water (3×100 mL), and the resulting organic layer was dried over magnesium sulphate, filtered, and concentrated to provide 7-(azidomethyl)-3-{[4-(methyloxy)phenyl]methyl}-7-{[(phenylmethyl)oxy]methyl}-1-oxa-3-azaspiro[4.5]decan-2-one (4.78 g, 89% crude yield) which was used without further purification. MS (m/z) 451.0 (M+H+).

Workup

  1. temperatureAfter 4 days the reaction was cooled to RT
  2. washThis mixture was washed with water (3×100 mL)
  3. dry with materialthe resulting organic layer was dried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-78b4781c01a340a0b2f119091db1b645
Source dataset
uspto-grants-2015_11
Patent number
US09187464B2

Reaction notes

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