Ammonium Chloride → Tert-butyl 3-(2-fluorobenzyl)-3-hydroxycyclohexylcarbamate

HRID 530839Notes

Reaction equation

HRID 530839 reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][CH2:5][CH:4]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:3]1.[F:16][C:17]1[CH:25]=[CH:24][CH:23]=[CH:22][C:18]=1[CH2:19][Mg]Br.[NH4+].[Cl-]>C(OCC)C>[F:16][C:17]1[CH:25]=[CH:24][CH:23]=[CH:22][C:18]=1[CH2:19][C:2]1([OH:1])[CH2:7][CH2:6][CH2:5][CH:4]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:12])([CH3:14])[CH3:13])[CH2:3]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 44228975(3-Oxo-cyclohexyl)-carbamic acid tert-butyl esterHCID 178505626HCID 178505626, compound

Product 1

HCID 67983409Tert-butyl 3-(2-fluorobenzyl)-3-hydroxycyclohexylcarbamate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of tert-butyl 3-oxocyclohexylcarbamate (2 mmol, 426 mg) in ethyl ether (10 mL) was added a solution of (2-fluorobenzyl)magnesium bromide in ether (5 mmol, 0.25 M, 20 mL) at 0° C. The reaction mixture was allowed to warm to room temperature and stirred for overnight. The reaction mixture was added to the NH4Cl aqueous solution. The organics were extracted with EtOAc. The EtOAc solution was concentrated. The product, tert-butyl 3-(2-fluorobenzyl)-3-hydroxycyclohexylcarbamate was purified by column chromatography on silica gel.

Workup

  1. extractionThe organics were extracted with EtOAc
  2. concentrationThe EtOAc solution was concentrated
  3. customThe product, tert-butyl 3-(2-fluorobenzyl)-3-hydroxycyclohexylcarbamate was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-14bd62da0f6a4a509fc40a1b6d0c9bb2
Source dataset
uspto-grants-2016_05
Patent number
US09351965B2

Reaction notes

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