Methanol → HCID 178495626, compound

HRID 731423Notes

Reaction equation

HRID 731423 reaction equation
Cl.[CH3:2][O:3][CH2:4][C@H:5]1[CH2:10][CH2:9][C@H:8]([NH2:11])[CH2:7][CH2:6]1.[C:12]1(=O)[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1.CO.C([BH3-])#N.[Na+]>C1COCC1>[CH:12]1([NH:11][C@H:8]2[CH2:9][CH2:10][C@H:5]([CH2:4][O:3][CH3:2])[CH2:6][CH2:7]2)[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

6

Reactant 4

HCID 887MethanolHCID 7967CyclohexanoneHCID 5003444Sodium cyanoborohydrideHCID 178495631HCID 178495631, compound

Product 1

HCID 178495626HCID 178495626, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of trans-4-methoxymethyl-cyclohexylamine hydrochloride (0.7 g), cyclohexanone (0.4 g), diisoropylethylamine (0.5 g) and molecular sieves (3 g) in THF (5 mL) and methanol (5 mL) was added sodium cyanoborohydride (0.49 g) and the mixture stirred overnight at room temperature. Insoluble material was removed by filtration and the crude product purified by flash chromatography to give cyclohexyl-(trans-4-methoxymethyl-cyclohexyl)-amine (0.29 g).

Workup

  1. customInsoluble material was removed by filtration
  2. customthe crude product purified by flash chromatography

Sources & evidence

ORD record
ord-5e3c3d42cc7f42fd9f1d78ac657dc760
Source dataset
uspto-grants-2009_09
Patent number
US07582769B2

Reaction notes

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