Cyclohexene oxide → HCID 86594080, compound

HRID 348540Notes

Reaction equation

HRID 348540 reaction equation
[OH:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@H:3]1[N:8]1[CH2:13][CH2:12][C:11](=[O:14])[CH2:10][CH2:9]1.[O:15]1C2(CCNCC2)O[CH2:17][CH2:16]1.C12OC1CCCC2>C(O)C>[O:15]1[C:11]2([CH2:12][CH2:13][N:8]([C@@H:3]3[CH2:4][CH2:5][CH2:6][CH2:7][C@H:2]3[OH:1])[CH2:9][CH2:10]2)[O:14][CH2:17][CH2:16]1

Participants

5

Reactant 3

HCID 9246Cyclohexene oxideHCID 674351,4-Dioxa-8-azaspiro(4.5)decaneHCID 86594081HCID 86594081, compound

Product 1

HCID 86594080HCID 86594080, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Preparation of (+/−)-trans-1-(2-hydroxy-cyclohexyl)-piperidin-4-one. To a solution of 1,4-dioxa-8-azaspiro[4,5]decane (14.7 g, 100 mmol) in ethanol (75 ml) was added cyclohexene oxide (10.0 g, 100 mmol). The reaction mixture was refluxed for 40 hours then cooled to room temperature and concentrated. The residue was chromatographed over silica gel (hexane/ethylacetate 4:1) to provide (+/−)-trans-2-(1,4-dioxa-8-aza-spiro[4.5]dec-8-yl)-cyclohexanol (22.1 g, 91%) as a white solid, MS (ISP): m/e=241.2 (M+).

Workup

  1. temperatureThe reaction mixture was refluxed for 40 hours
  2. concentrationconcentrated
  3. customThe residue was chromatographed over silica gel (hexane/ethylacetate 4:1)

Sources & evidence

ORD record
ord-91aa3938c7254a6695ef83b2b0f6eee0
Source dataset
uspto-grants-2007_02
Patent number
US07176316B2

Reaction notes

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