1,2-Dichlorobenzene → HCID 117985969, compound

HRID 1055502Notes

Reaction equation

HRID 1055502 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][CH3:49])=[CH:43][CH:42]=4)[CH:34]=3)[O:32][C@@:10]1([CH:50]([OH:52])[CH3:51])[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]([CH:50]([OH:52])[CH3:51])([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:42]=[CH:43][C:44]([O:47][CH2:48][CH3:49])=[CH:45][CH:46]=1

Participants

5

Reactant 2

HCID 72391,2-DichlorobenzeneHCID 118377829HCID 118377829, compound

Product 1

HCID 117985969HCID 117985969, compoundYield 51.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of 1-[(1R,2S,3S,4R,5S)-2,3,4-tribenzyloxy-5-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6,8-dioxabicyclo[3.2.1]octan-1-yl]ethanol 1m (1.71 g, 2.36 mmol) in a methanol/tetrahydrofuran mixture (v/v=4/1, 30 mL) were added o-dichlorobenzene (1.74 g, 11.8 mmol) and 10% Pd/C (250 mg, 0.236 mmol) at room temperature. The mixture was stirred under H2 at room temperature for 1.5 hours and filtered. The filtrate was concentrated in vacuo. The residue was purified by preparative HPLC (prep-HPLC) to give the title compound 1 as a white solid (544 mg, 51.3%, HPLC: 99.6%). The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 451.2 [M+H]+; and 1H NMR (400 MHz, CDCl3) δ (ppm): 7.35 (m, 1H), 7.29-7.21 (m, 2H), 7.04 (m, 2H), 6.75 (m, 2H), 4.71 (br, 1H), 4.51 (br, 1H), 4.14 (m, 1H), 4.01 (m, 3H), 3.98 (m, 2H), 3.89 (m, 1H), 3.77 (m, 2H), 3.60 (m, 1H), 3.52 (br, 1H), 3.06 (br, 1H), 1.34 (t, 3H), 0.91 (d, 3H).

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated in vacuo
  3. customThe residue was purified by preparative HPLC (prep-HPLC)

Sources & evidence

ORD record
ord-53a00ada24be4f6e94d6777b4e9d9172
Source dataset
uspto-grants-2016_07
Patent number
US09394329B2

Reaction notes

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