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Trifluoroacetic acid → 13-Oxa-6-azadispiro[4.1.5.2]tetradecane

HRID 276257
Notes
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Reaction equation

HRID 276257 reaction equation
[NH2:1][C:2]1([CH2:7][OH:8])[CH2:6][CH2:5][CH2:4][CH2:3]1.C(O)(C(F)(F)F)=O.[C:16]1(=O)[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1.S([O-])([O-])(=O)=O.[Na+].[Na+]>C(Cl)Cl>[CH2:6]1[C:2]2([NH:1][C:16]3([CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]3)[O:8][CH2:7]2)[CH2:3][CH2:4][CH2:5]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 7967CyclohexanoneHCID 24436Sodium SulfateHCID 663071-Aminocyclopentanemethanol

Product 1

HCID 1831620513-Oxa-6-azadispiro[4.1.5.2]tetradecaneYield 97.2%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Conditions

Temperature
20 °C

Procedure

To a solution of 1-amino-1-(hydroxymethyl)cyclopentane (Method B1c; 1.44 g, 12.54 mmol) in CH2Cl2 (10 mL) at 4° C. was added TFA (0.097 mL, 1.25 mmol), cyclohexanone (1.30 mL, 12.54 mmol) and sodium sulfate (2 g) and the reaction was warmed to 20° C. The reaction was stirred for 72 h and was sequentially washed with water (10 mL) and a saturated NaHCO3 solution (20 mL), dried (MgSO4), and concentrated under reduced pressure to give 14-aza-7-oxadispiro[4.2.5.1]tetradecane (2.38 g, 97%): GC-MS m/z 195 (M+).

Workup

  1. washwas sequentially washed with water (10 mL)
  2. dry with materiala saturated NaHCO3 solution (20 mL), dried (MgSO4)
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-10912cbbf8d74539bbc4ed2bcc173491
Source dataset
uspto-grants-2002_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06353006B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes