Benzyl Bromide → 1-Boc-4-(hydroxymethyl)-4-[(benzyloxy)methyl]piperidine

HRID 2213029Notes

Reaction equation

HRID 2213029 reaction equation
[OH-].[K+].[OH:3][CH2:4][C:5]1([CH2:18][OH:19])[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]1.C1OCCOCCOCCOCCOCCOC1.[CH2:38](Br)[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>O1CCCC1.[Cl-].[Na+].O>[OH:3][CH2:4][C:5]1([CH2:18][O:19][CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:15])([CH3:16])[CH3:17])=[O:12])[CH2:7][CH2:6]1

Participants

7

Reactant 4

HCID 7498Benzyl BromideHCID 14797Potassium HydroxideHCID 2855718-Crown-6HCID 21955203Tert-butyl 4,4-bis(hydroxymethyl)piperidine-1-carboxylate

Product 1

HCID 219551981-Boc-4-(hydroxymethyl)-4-[(benzyloxy)methyl]piperidineYield 40.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Finely ground potassium hydroxide (248 mg, 44 mmol) was added to a stirred, cooled (10° C.) solution of 1,1-dimethylethyl 4,4-bis(hydroxymethyl)-1-piperidinecarboxylate (Description 67, 1.83 g, 7.4 mmol), 18-crown-6 (196 mg, 0.74 mmol) and benzyl bromide (884 μL, 7.4 mmol) in tetrahydrofuran (80 mL) and the mixture was stirred at room temperature for 16 hours. Brine (40 mL) was added and the layers were separated. The organic layer was dried (MgSO4) and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel, eluting with isohexane/EtOAc (80:20 increasing to 50:50) to give the title compound (1.0 g, 40%). m/z (ES+) 336 (M+1).

Workup

  1. customthe layers were separated
  2. dry with materialThe organic layer was dried (MgSO4)
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by flash column chromatography on silica gel
  5. washeluting with isohexane/EtOAc (80:20 increasing to 50:50)

Sources & evidence

ORD record
ord-6bd62ae675fc4adca9448695bd9a5e67
Source dataset
uspto-grants-2006_09
Patent number
US07105507B2

Reaction notes

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