Sodium Carbonate → (S)-ethyl 2-(1-(4-chlorophenyl)-3-methyl-6-(trifluoromethylsulfonyloxy) naphthalen-2-yl)-2-hydroxyacetate

HRID 514059Notes

Reaction equation

HRID 514059 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3[C:12](=[CH:13][C:14]([O:18][S:19]([C:22]([F:25])([F:24])[F:23])(=[O:21])=[O:20])=[CH:15][CH:16]=3)[CH:11]=[C:10]([CH3:26])[C:9]=2[C:27](=[O:33])[C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:4][CH:3]=1.B1(C)OC(C2C=CC=CC=2)(C2C=CC=CC=2)[C@@H]2N1CCC2.[B]1OC2C(=CC=CC=2)O1.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:17]3[C:12](=[CH:13][C:14]([O:18][S:19]([C:22]([F:25])([F:24])[F:23])(=[O:21])=[O:20])=[CH:15][CH:16]=3)[CH:11]=[C:10]([CH3:26])[C:9]=2[C@H:27]([OH:33])[C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 6327445BenzcatechinboraneHCID 9838490(R)-2-Methyl-CBS-oxazaborolidineHCID 86691547Ethyl 2-(1-(4-chlorophenyl)-3-methyl-6-(trifluoromethylsulfonyloxy)naphthalen-2-yl)-2-oxoacetate

Product 1

HCID 86691546(S)-ethyl 2-(1-(4-chlorophenyl)-3-methyl-6-(trifluoromethylsulfonyloxy) naphthalen-2-yl)-2-hydroxyacetate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a solution of ethyl 2-(1-(4-chlorophenyl)-3-methyl-6-(trifluoromethylsulfonyloxy)naphthalen-2-yl)-2-oxoacetate (1 g, 2 mmol) and (R)-(+)-2-methyl-CBS-oxazaborolidine (0.11 g, 0.4 mmol) in toluene (7 mL) cooled to −20° C. was added a solution of freshly distilled catecholborane (0.29 mL, 2.6 mmol) in toluene (3 mL). After 3 h, saturated Na2CO3 (10 mL) was added, the mixture allowed to warm to room temperature and the layers separated. Following extraction with EtOAc, the combined organic layers were washed with additional saturated Na2CO3 (15 mL portions) until the washing was no longer colored and then once with saturated NH4Cl (15 mL). After drying over anhydrous MgSO4, the solution was absorbed onto silica gel in vacuo and purified by Yamazen column chromatography (10-65% EtOAc/Hex) to afford 0.61 g (61%, 98% ee) of the title compound as a colorless amorphous solid. 1H-NMR: 400 MHz, (CDCl3) δ: 7.72 (s, 1H); 7.69 (d, J=2.4 Hz, 1H); 7.50 (m, 2H); 7.37 (d, J=9.2 Hz, 1H); 7.30 (m, 2H); 7.19 (dd, J=9.2, 2.4 Hz, 1H); 5.21 (d, J=2 Hz, 1H); 4.21 (m, 2H); 3.25 (d, J=2 Hz, 1H); 2.53 (s, 3H); 1.22 (t, J=7.2 Hz, 3H).

Workup

  1. customthe layers separated
  2. extractionextraction with EtOAc
  3. washthe combined organic layers were washed with additional saturated Na2CO3 (15 mL portions) until the washing
  4. dry with materialAfter drying over anhydrous MgSO4
  5. customthe solution was absorbed onto silica gel in vacuo
  6. custompurified by Yamazen column chromatography (10-65% EtOAc/Hex)

Sources & evidence

ORD record
ord-c8a13706579a46b2bfc9d7fc36059ebd
Source dataset
uspto-grants-2015_08
Patent number
US09102614B2

Reaction notes

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