Diethyl Ether → Tert-butyl 4-(4-chlorophenyl)-4-hydroxyazepane-1-carboxylate

HRID 242538Notes

Reaction equation

HRID 242538 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][CH2:12][C:11](=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([Mg]Br)=[CH:19][CH:18]=1.C(OCC)C>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][CH2:12][C:11]([C:20]2[CH:21]=[CH:22][C:17]([Cl:16])=[CH:18][CH:19]=2)([OH:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 1512679N-Boc-hexahydro-1H-azepin-4-oneHCID 178478191HCID 178478191, compound

Product 1

HCID 18675706Tert-butyl 4-(4-chlorophenyl)-4-hydroxyazepane-1-carboxylateYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a cold (0° C.) stirred solution of 1-t-butoxycarbonyl-4-oxohomopiperidine (1.42 g, 6.07 mmol) in anhydrous THF (50 mL) under argon was added dropwise 1.0 M 4-chlorophenylmagnesium bromide in diethyl ether (10 mL, 10 mmol). The reaction was warmed to RT for 2 hrs then quenched with sat'd aqueous NH4Cl (5 mL). The reaction mixture was extracted with EtOAc (2×50 mL), the organic layers combined and dried over Na2SO4. Pure 1-t-butoxycarbonyl-4-(4-chlorophenyl)-4-hydroxyhomopiperidine (2.1 g, 96%) was isolated via silica gel flash chromatography eluting with 50% EtOAc/hexane. 1H NMR CDCl3 δ 1.43 (9H, s), 1.61-2.22 (6H, m), 3.21-3031 (2H, m), 3.48-3.82 (2H, m).

Workup

  1. customthen quenched with sat'd aqueous NH4Cl (5 mL)
  2. extractionThe reaction mixture was extracted with EtOAc (2×50 mL)
  3. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-24ad239a2b764d218c4350de8dc27dd3
Source dataset
uspto-grants-2014_02
Patent number
US08653096B2

Reaction notes

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