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N,N,N-Tributylbutan-1-aminium fluoride--hydrogen fluoride (1/1/2) → Tert-butyl 4-[(benzyloxy)methyl]-3-fluoro-4-hydroxypiperidine-1-carboxylate

HRID 70789
Notes
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Reaction equation

HRID 70789 reaction equation
[F:1][H-]F.[K+].CCCC[N+](CCCC)(CCCC)CCCC.F.F.[F-].[CH2:25]([O:32][CH2:33][C:34]12[O:40][CH:39]1[CH2:38][N:37]([C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[CH2:36][CH2:35]2)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C(Cl)(Cl)Cl>[CH2:25]([O:32][CH2:33][C:34]1([OH:40])[CH2:35][CH2:36][N:37]([C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[CH2:38][CH:39]1[F:1])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11748636N,N,N-Tributylbutan-1-aminium fluoride--hydrogen fluoride (1/1/2)HCID 86677053Tert-butyl 6-[(benzyloxy)methyl]-7-oxa-3-azabicyclo[4.1.0]heptane-3-carboxylateHCID 178506425HCID 178506425, compound

Product 1

HCID 71268614Tert-butyl 4-[(benzyloxy)methyl]-3-fluoro-4-hydroxypiperidine-1-carboxylateYield 66.3%

Reagents, catalysts & solvents 1

HCID 6212
Chloroform
Solvent

Conditions

Temperature
120 °C

Procedure

Potassium bifluoride (1.22 g) and tetrabutylammonium dihydrogentrifluoride (472 mg) were added to tert-butyl 6-[(benzyloxy) methyl]-7-oxa-3-azabicyclo[4.1.0]heptane-3-carboxylate (2.50 g), followed by heating and stirring at 120° C. for 2 days. The reaction was diluted with chloroform and filtered through Celite. The residue obtained by concentration of the solvent under reduced pressure was purified by silica gel column chromatography (EtOAc/hexane) to obtain tert-butyl 4-[(benzyloxy)methyl]-3-fluoro-4-hydroxypiperidine-1-carboxylate (1.76 g).

Workup

  1. temperatureby heating
  2. filtrationfiltered through Celite
  3. customThe residue obtained by concentration of the solvent under reduced pressure
  4. customwas purified by silica gel column chromatography (EtOAc/hexane)

Sources & evidence

ORD record
ord-50961c977c3c40c8a5ece1e330f477df
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08822688B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes