Hydrochloric Acid → 8-Benzyl-9,9-dimethyl-11-oxa-3,8-diazaspiro[5.5]undecane hydrochloride

HRID 73051Notes

Reaction equation

HRID 73051 reaction equation
[CH2:1]([N:8]1[C:25]([CH3:27])([CH3:26])[CH2:24][O:23][C:10]2([CH2:15][CH2:14][N:13](C(OC(C)(C)C)=O)[CH2:12][CH2:11]2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:28].O1CCOCC1>>[ClH:28].[CH2:1]([N:8]1[C:25]([CH3:27])([CH3:26])[CH2:24][O:23][C:10]2([CH2:11][CH2:12][NH:13][CH2:14][CH2:15]2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 70872658Tert-butyl 8-benzyl-9,9-dimethyl-11-oxa-3,8-diazaspiro[5.5]undecane-3-carboxylate

Product 1

HCID 708725958-Benzyl-9,9-dimethyl-11-oxa-3,8-diazaspiro[5.5]undecane hydrochlorideYield 86%

Procedure

Tert-butyl 8-benzyl-9,9-dimethyl-11-oxa-3,8-diazaspiro[5.5]undecane-3-carboxylate (89 mg, 0.24 mmol) was treated with hydrogen chloride solution in dioxane (240 μL of 4 M, 0.95 mmol). The reaction mixture was stirred for 18 h. The reaction mixture was concentrated in vacuo to provide 8-benzyl-9,9-dimethyl-11-oxa-3,8-diazaspiro[5.5]undecane hydrochloride (56 mg, 86%). ESI-MS m/z calc. 274.4. Found 275.5 (M+1)+; Retention time: 0.80 minutes (3 min run).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-640b2053ccb14bc19f775b1b136d97e1
Source dataset
uspto-grants-2014_09
Patent number
US08828996B2

Reaction notes

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