Ammonium Chloride → cis-4-(Boc-amino)-1-methylcyclohexanol

HRID 1893395Notes

Reaction equation

HRID 1893395 reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][CH:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:4][CH2:3]1.[CH3:16][Mg+].[Br-].[NH4+].[Cl-]>C1COCC1>[OH:1][C:2]1([CH3:16])[CH2:3][CH2:4][CH:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:12])([CH3:14])[CH3:13])[CH2:6][CH2:7]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 1512535tert-butyl N-(4-oxocyclohexyl)carbamateHCID 178418689HCID 178418689, compound

Product 1

HCID 21877240cis-4-(Boc-amino)-1-methylcyclohexanolYield 56.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of tert-butyl 4-oxocyclohexylcarbamate (2 g, 9.3 mmol) in THF (40 mL) at −78° C. was added dropwise MeMgBr (10 mL of 3M/THF, 30 mmol). The reaction mixture was allowed to warm to room temperature. After stirring at room temperature for 18 h, the reaction was treated with saturated NH4Cl aqueous solution. The solution was concentrated, taken up into CH2Cl2, washed with H2O by aid of citric acid. The organic phase was washed with saturated NaHCO3 aqueous solution, H2O, brine, dried (Na2SO4) and concentrated. The crude product was purified by column chromatography to give tert-butyl 4-hydroxy-4-methylcyclohexylcarbamate 2 as oil (1.2 g, 56%). 1H NMR (300 MHz, CDCl3) δ 1.20 (s, 3H), 1.45 (s, overlapped 9H), 1.5˜1.8 (set of m, 10H), 3.40 (br, 1H), 4.40 (br, 1H).

Workup

  1. concentrationThe solution was concentrated
  2. washwashed with H2O by aid of citric acid
  3. washThe organic phase was washed with saturated NaHCO3 aqueous solution, H2O, brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-277f890ad5d94babad85dd3385d38f78
Source dataset
uspto-grants-2013_08
Patent number
US08513242B2

Reaction notes

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