Ethanol → HCID 68154419, compound

HRID 73612Notes

Reaction equation

HRID 73612 reaction equation
[CH2:1]([N:8]([CH2:21][C:22]#N)[C@@H:9]1[CH2:14][CH2:13][CH2:12][CH2:11][C@@:10]1([C:16]([O:18][CH2:19][CH3:20])=C)[OH:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:24]([OH:26])[CH3:25]>[N+]([O-])([O-])=O.[Ag+]>[CH2:1]([N:8]1[C@H:9]2[C@:10]([OH:15])([CH2:11][CH2:12][CH2:13][CH2:14]2)[C:16]([O:26][CH2:24][CH3:25])([O:18][CH2:19][CH3:20])[CH2:22][CH2:21]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 702Ethanol2×HCID 86668652HCID 86668652, compound

Product 1

HCID 68154419HCID 68154419, compound

Reagents, catalysts & solvents 1

HCID 24470Silver NitrateCatalyst2×

Procedure

To silver nitrate (125 mg, 0.735 mmol) in Ethanol (27.00 ml) at room temperature was added {Benzyl[(1R,2R)-2-(1-ethoxyethenyl)-2-hydroxycyclohexyl]amino}acetonitrile (220 mg, 0.700 mmol) in 10 ml of absolute ethanol. The reaction mixture was stirred for an addition 1 hr. Another 125 mg of Silver Nitrate was added and the reaction was stirred overnight. The reaction mixture was filtered through a pad of celite, concentrated. The residue was purified by column chromatography (dry load) on silica gel, eluting with CH2Cl2/MeOH/NH3(Aq.) to give the title compound. 1H-NMR (500 MHz, CDCl3) 2-4: δ 7.20-7.36 (m, 5H), 4.07 (d, 1H), 3.74 (dt, 1H), 3.62 (dt, 1H), 3.52 (dt, 1H), 3.41 (dt, 1H), 3.28 (bs, 1H), 3.06 (d, 1H), 2.61 (m, 1H), 2.00-2.14 (m, 2H), 1.88-1.98 (m, 2H), 1.70-1.80 (m, 2H), 1.54-1.62 (m, 2H), 1.22-1.44 (m, 2H), 1.18 (t, 6H). LRMS m/z (M+H) Calcd:334.5. found: 334.5.

Workup

  1. stirringthe reaction was stirred overnight
  2. filtrationThe reaction mixture was filtered through a pad of celite
  3. concentrationconcentrated
  4. customThe residue was purified by column chromatography (dry load) on silica gel
  5. washeluting with CH2Cl2/MeOH/NH3(Aq.)

Sources & evidence

ORD record
ord-21b40a1fdc084526a38d79e8d5891700
Source dataset
uspto-grants-2014_09
Patent number
US08829196B2

Reaction notes

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