Dimethylformamide → HCID 178511088, compound

HRID 712122Notes

Reaction equation

HRID 712122 reaction equation
CC1C=CC(S(O[CH2:12][C@H:13]2[CH2:18][CH2:17][C@@H:16]([OH:19])[CH2:15][CH2:14]2)(=O)=O)=CC=1.[C-]#N.[Na+].[CH3:23][N:24](C=O)C>C(OCC)(=O)C.O>[OH:19][C@@H:16]1[CH2:15][CH2:14][C@H:13]([CH2:12][C:23]#[N:24])[CH2:18][CH2:17]1

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 8929Sodium CyanideHCID 178427757HCID 178427757, compound

Product 1

HCID 178511088HCID 178511088, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of (cis-4-hydroxycyclohexyl)methyl 4-methylbenzenesulfonate (6.9 g, 24 mmol) (first fraction from last step), sodium cyanide (1.43 g, 29.1 mmol) and DMF (86 mL) was stirred at 80° C. for 1 h. After cooling to room temperature, the mixture was diluted with ethyl acetate and water. The aqueous layer was extracted with ethyl acetate once. The combined organic layers were dried over Na2SO4 and concentrated. The crude was purified with flash chromatography (eluting with a gradient of 0-50% ethyl acetate in hexanes) to give the desired product (2.5 g, 74%). 1H NMR (300 MHz, CDCl3) δ 3.58 (m, 1H), 2.27 (d, J=6.3 Hz, 2H), 2.02 (m, 2H), 1.88 (m, 2H), 1.78-1.45 (m, 2H), 1.42-1.07 (m, 4H) ppm.

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionThe aqueous layer was extracted with ethyl acetate once
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. concentrationconcentrated
  5. customThe crude was purified with flash chromatography (
  6. washeluting with a gradient of 0-50% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-6a87c0fa611a4e568901a2e2afa0d664
Source dataset
uspto-grants-2015_11
Patent number
US09181271B2

Reaction notes

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