Ethanol → HCID 58828635, compound

HRID 1711405Notes

Reaction equation

HRID 1711405 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([O:17][C:18]2[CH:23]=[CH:22][C:21]([N+:24]([O-])=O)=[C:20]([CH2:27][S:28]([C:31]3[C:40]4[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=4)[CH:34]=[CH:33][CH:32]=3)(=[O:30])=[O:29])[CH:19]=2)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)C.O.O.[Sn](Cl)Cl>C(OCC)(=O)C>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([O:17][C:18]2[CH:23]=[CH:22][C:21]([NH2:24])=[C:20]([CH2:27][S:28]([C:31]3[C:40]4[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=4)[CH:34]=[CH:33][CH:32]=3)(=[O:30])=[O:29])[CH:19]=2)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 61436Stannous chloride dihydrateHCID 58828629HCID 58828629, compound

Product 1

HCID 58828635HCID 58828635, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
75 °C

Procedure

A solution of 4-[3-(1-naphthylsulfonylmethyl)-4-nitrophenoxy]piperidin-1-ylcarboxylic acid benzyl ester (3.90 g, 6.96 mmol) in ethyl acetate was treated sequentially with ethanol and tin (II) chloride dihydrate (24.0 g, 106 mmol), stirred at 75° C. under nitrogen for 3 hours and concentrated in vacuo. The resultant residue was partitioned in ethyl acetate and water. The phases were separated; the organic phase was washed with 2.5 N sodium hydroxide and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo for 20 minutes at 78° C. to yield 4-[4-amino-3-(naphthalene-1-sulfonylmethyl)-phenoxy]-piperidine-1-carboxylic acid benzyl ester as a dark yellow film, 3.3 g (89% yield), Mass spectrum (+EI, [M+H]+) m/z 531. 1HNMR (500 MHz, DMSO-d6): δ8.57 (d, 1H, J=8.54 Hz), 8.24 (d, 1H, J=8.17 Hz), 8.03-8.06 (m, 1H), 8.00 (dd, 1H, J=7.44 Hz and 1.22 Hz), 7.58-7.69 (m, 3H), 7.27-7.38 (m, 5H), 6.53-6.58 (m, 2H), 5.97 (d, 1H, J=2.56 Hz), 5.04 (s, 2H), 4.71 (s, 2H), 4.64 (s, 2H), 3.61-3.66 (m, 1H), 3.47-3.53 (m, 2H), 2.99-3.05 (m, 2H), 1.43-1.48 (m, 2H), 1.10-1.19 ppm (m, 2H).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe resultant residue was partitioned in ethyl acetate
  3. customThe phases were separated
  4. washthe organic phase was washed with 2.5 N sodium hydroxide and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated in vacuo for 20 minutes at 78° C.

Sources & evidence

ORD record
ord-3fc3cf93df1a42bc92dc3de21312b904
Source dataset
uspto-grants-2010_09
Patent number
US07790751B2

Reaction notes

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