Hydrochloric Acid → 8-But-2-ynyl-10,10-difluoro-11-oxa-3,8-diazaspiro[5.5]undecane

HRID 712996Notes

Reaction equation

HRID 712996 reaction equation
[CH2:1]([N:5]1[CH2:22][C:21]([F:24])([F:23])[O:20][C:7]2([CH2:12][CH2:11][N:10](C(OC(C)(C)C)=O)[CH2:9][CH2:8]2)[CH2:6]1)[C:2]#[C:3][CH3:4].Cl.O1CCOCC1.C([O-])([O-])=O.[K+].[K+]>ClCCl.C(Cl)Cl.C(#N)C>[CH2:1]([N:5]1[CH2:22][C:21]([F:23])([F:24])[O:20][C:7]2([CH2:8][CH2:9][NH:10][CH2:11][CH2:12]2)[CH2:6]1)[C:2]#[C:3][CH3:4]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 70872876Tert-butyl 8-but-2-ynyl-10,10-difluoro-11-oxa-3,8-diazaspiro[5.5]undecane-3-carboxylate

Product 1

HCID 682912038-But-2-ynyl-10,10-difluoro-11-oxa-3,8-diazaspiro[5.5]undecaneYield 96%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21877088Acetonitrile methylene chlorideSolvent

Procedure

Tert-butyl 8-but-2-ynyl-10,10-difluoro-11-oxa-3,8-diazaspiro[5.5]undecane-3-carboxylate (50.0 mg, 0.145 mmol) was dissolved in dichloromethane (1 mL) and treated with HCl in dioxane (1.3 mL of 4 M, 5.1 mmol). The reaction mixture was stirred for 1 h then concentrated in vacuo several times with acetonitrile to yield a white solid. The solid was dissolved in 1:1 DCM/acetonitrile and stirred with solid K2CO3 for 1 h. The mixture was filtered and concentrated to provide 8-but-2-ynyl-10,10-difluoro-11-oxa-3,8-diazaspiro[5.5]undecane (34 mg, 96%). ESI-MS m/z calc. 244.1. found 245.3 (M+1)+; Retention time: 0.79 minutes (3 min run).

Workup

  1. concentrationthen concentrated in vacuo several times with acetonitrile
  2. customto yield a white solid
  3. filtrationThe mixture was filtered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-620ec660c52842bb9040238bd6c2cd50
Source dataset
uspto-grants-2015_11
Patent number
US09181273B2

Reaction notes

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