1,2-Dichlorobenzene → HCID 117986015, compound

HRID 1055559Notes

Reaction equation

HRID 1055559 reaction equation
C([O:8][C@H:9]1[C@H:15]([O:16]CC2C=CC=CC=2)[C@@H:14]([O:24]CC2C=CC=CC=2)[C@:13]2([C:33]3[CH:38]=[CH:37][C:36]([Cl:39])=[C:35]([CH2:40][C:41]4[CH:46]=[CH:45][C:44]([O:47][CH2:48][C:49]([F:52])([F:51])[F:50])=[CH:43][CH:42]=4)[CH:34]=3)[O:32][C@@:10]1([C:53]([OH:56])([CH3:55])[CH3:54])[CH2:11][O:12]2)C1C=CC=CC=1.ClC1C=CC=CC=1Cl>[Pd].CO.O1CCCC1>[Cl:39][C:36]1[CH:37]=[CH:38][C:33]([C@@:13]23[O:32][C@@:10]([C:53]([OH:56])([CH3:55])[CH3:54])([CH2:11][O:12]2)[C@@H:9]([OH:8])[C@H:15]([OH:16])[C@H:14]3[OH:24])=[CH:34][C:35]=1[CH2:40][C:41]1[CH:46]=[CH:45][C:44]([O:47][CH2:48][C:49]([F:51])([F:50])[F:52])=[CH:43][CH:42]=1

Participants

5

Reactant 2

HCID 72391,2-DichlorobenzeneHCID 118377945HCID 118377945, compound

Product 1

HCID 117986015HCID 117986015, compoundYield 60.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of 2-[(1S,2S,3S,4R,5S)-2,3,4-tribenzyloxy-5-[4-chloro-3-[[4-(2,2,2-trifluoroethoxyl) phenyl]methyl]phenyl]-6,8-dioxabicyclo[3.2.1]octan-1-yl]propan-2-ol 18c (156 mg, 0.20 mmol) in a methanol/tetrahydrofuran mixture (v/v=4/1, 15 mL) were added o-dichlorobenzene (0.11 mL, 0.99 mmol) and 10% Pd/C (21.0 mg, 0.02 mmol) at room temperature. The mixture was stirred at room temperature for 2 hours under H2 and filtered. The filtrate was concentrated in vacuo. The residue was purified by silica gel chromatography eluted with PE/EtOAc(v/v)=1/1 to give the title compound 18 as pale yellow oil (62.5 mg, 62.5%, HPLC: 95.60%). The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 563.3 [M+CHOO]−; and 1H NMR (600 MHz, DMSO-d6) δ(ppm): 7.43 (d, 1H), 7.39 (d, 1H), 7.33 (d, 1H), 7.15 (q, 2H), 6.97 (q, 2H), 4.70 (q, 2H), 4.02 (m, 3H), 3.80 (d, 1H), 3.70 (d, 1H), 3.45 (m, 2H), 1.20 (s, 3H), 1.15 (s, 3H).

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated in vacuo
  3. customThe residue was purified by silica gel chromatography
  4. washeluted with PE/EtOAc(v/v)=1/1

Sources & evidence

ORD record
ord-2084472f47c841ddb7013ce3bd874baf
Source dataset
uspto-grants-2016_07
Patent number
US09394329B2

Reaction notes

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