Hydrochloric Acid → 4-(2,2-Difluoropropyl)-2-(methoxymethyl)-1-oxa-4,9-diazaspiro[5.5]undecane hydrochloride

HRID 713005Notes

Reaction equation

HRID 713005 reaction equation
[F:1][C:2]([F:26])([CH3:25])[CH2:3][N:4]1[CH2:21][CH:20]([CH2:22][O:23][CH3:24])[O:19][C:6]2([CH2:11][CH2:10][N:9](C(OC(C)(C)C)=O)[CH2:8][CH2:7]2)[CH2:5]1.[ClH:27].O1CCOCC1>>[ClH:27].[F:26][C:2]([F:1])([CH3:25])[CH2:3][N:4]1[CH2:5][C:6]2([CH2:11][CH2:10][NH:9][CH2:8][CH2:7]2)[O:19][CH:20]([CH2:22][O:23][CH3:24])[CH2:21]1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 70872823Tert-butyl 8-(2,2-difluoropropyl)-10-(methoxymethyl)-11-oxa-3,8-diazaspiro[5.5]undecane-3-carboxylate

Product 1

HCID 682912054-(2,2-Difluoropropyl)-2-(methoxymethyl)-1-oxa-4,9-diazaspiro[5.5]undecane hydrochlorideYield 99%

Procedure

Tert-butyl 8-(2,2-difluoropropyl)-10-(methoxymethyl)-11-oxa-3,8-diazaspiro[5.5]undecane-3-carboxylate (77.0 mg, 0.204 mmol) was treated with HCl in dioxane (509 μL of 4 M, 2.04 mmol) and stirred for 2 h. The solvent was evaporated to provide 4-(2,2-difluoropropyl)-2-(methoxymethyl)-1-oxa-4,9-diazaspiro[5.5]undecane hydrochloride as yellow solid (64 mg, 0.20 mmol, 99%). ESI-MS m/z calc. 278.2. found 279.3 (M+1)+; Retention time: 0.79 minutes (3 min run).

Workup

  1. customThe solvent was evaporated

Sources & evidence

ORD record
ord-1438f006011746b9918c85a8e65bb54f
Source dataset
uspto-grants-2015_11
Patent number
US09181273B2

Reaction notes

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