Benzcatechinborane → HCID 86691579, compound

HRID 926207Notes

Reaction equation

HRID 926207 reaction equation
[CH3:1][C:2]1[C:3]([C:20](=[O:26])[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[C:4]([O:12][S:13]([C:16]([F:19])([F:18])[F:17])(=[O:15])=[O:14])[C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.B1(C)OC(C2C=CC=CC=2)(C2C=CC=CC=2)[C@@H]2N1CCC2.[B]1OC2C(=CC=CC=2)O1>C1(C)C=CC=CC=1>[OH:26][C@@H:20]([C:3]1[C:2]([CH3:1])=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]=1[O:12][S:13]([C:16]([F:19])([F:17])[F:18])(=[O:14])=[O:15])[C:21]([O:23][CH2:24][CH3:25])=[O:22]

Participants

5

Reactant 3

HCID 6327445BenzcatechinboraneHCID 9838490(R)-2-Methyl-CBS-oxazaborolidineHCID 86691578HCID 86691578, compound

Product 1

HCID 86691579HCID 86691579, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
-40 °C

Procedure

Ethyl 2-(3-methyl-1-(trifluoromethylsulfonyloxy)naphthalen-2-yl)-2-oxoacetate (1.31 g, 3.3 mmol) was dissolved in toluene (20 mL) and cooled to −40° C. After stirring for 20 minutes, (R)-(+)-2-Methyl-CBS-oxazaborolidine (219 mg, 7.5 mmol) and catecholborane (750 μL, 7.04 mmol) were added and the mixture stirred at −40° C. After 2 hrs at −40° C. the reaction was quenched by the addition of 15% Na2CO3 (12 mL) and the mixture was allowed to warm to room temperature. The mixture was washed with 15% Na2CO3 (8×12 mL) and saturated NH4Cl (24 mL), organic layer was dried with sodium sulfate, filtered and concentrated in vacuo. Chromatography using silica gel using EtOAc in hexanes produced the desired (S)-ethyl 2-hydroxy-2-(3-methyl-1-(trifluoromethylsulfonyloxy)naphthalen-2-yl)acetate. 1H-NMR: 400 MHz, (CDCl3): δ 8.08-8.06 (m, 1H); 7.81-7.79 (m, 1H); 7.69 (s, 1H); 7.60-7.57 (m, 2H); 5.81-5.80 (m, 1H); 4.35-4.19 (m, 2H); 3.42 (d, J=2.4 Hz, 1H); 2.50 (s, 3H); 1.21 (t, J=7.0 Hz, 3H).

Workup

  1. stirringthe mixture stirred at −40° C
  2. customAfter 2 hrs at −40° C. the reaction was quenched by the addition of 15% Na2CO3 (12 mL)
  3. temperatureto warm to room temperature
  4. washThe mixture was washed with 15% Na2CO3 (8×12 mL) and saturated NH4Cl (24 mL), organic layer
  5. dry with materialwas dried with sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b68aeb1cd6554ed4810665180a406f4e
Source dataset
uspto-grants-2016_03
Patent number
US09284323B2

Reaction notes

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