Boron Trichloride → HCID 86686872, compound

HRID 2406276Notes

Reaction equation

HRID 2406276 reaction equation
C([O:8][C@@H:9]1[C@H:13]([CH2:14][O:15]CC2C=CC=CC=2)[CH2:12][C@@H:11]([O:23][C:24]2[CH:29]=[C:28]([Cl:30])[N:27]=[CH:26][N:25]=2)[CH2:10]1)C1C=CC=CC=1.ClB(Cl)Cl>C(Cl)Cl>[Cl:30][C:28]1[N:27]=[CH:26][N:25]=[C:24]([O:23][C@H:11]2[CH2:10][C@H:9]([OH:8])[C@H:13]([CH2:14][OH:15])[CH2:12]2)[CH:29]=1

Participants

4

Reactant 2

HCID 25135Boron TrichlorideHCID 86686871HCID 86686871, compound

Product 1

HCID 86686872HCID 86686872, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

The crude intermediate 4-((1R,3S,4S)-3-(benzyloxy)-4-(benzyloxymethyl)cyclopentyloxy)-6-chloropyrimidine (25) was taken up in methylene chloride (3000 mL) and the mixture was cooled to 0° C. 1.0 M of Trichloro-borane in methylene chloride (1087.538 mL, 1087.538 mmol) was added slowly maintaining <10° C. The resulting mixture was allowed to stir for 1 hour at 0° C. HPLC analysis indicated consumption of starting material. The reaction mixture was added slowly to saturated sodium bicarbonate in water (2300 mL) and the biphasic mixture was allowed to stir for 20 minutes. The methylene chloride layer was separated and the aqueous extracted twice with methylene chloride (2300 mL). The organics were combined and concentrated. The residue was purified by eluting through a silica gel (1 kg) plug with 50 to 100% ethyl acetate/hexane (hexane (6 L)+ethyl acetate (14 L). The desired fractions were combined and concentrated to give a red solid (124 g, 70%). 1H NMR (300 MHz, CD3OD, δ): 8.58 (s, 1H), 6.91 (s, 1H), 5.61 (m, 1H), 4.39 (t, 1H), 3.75 (m, 1H), 3.61 (m, 1H), 2.25 (m, 3H) and 2.00 (m, 2H)

Workup

  1. temperaturemaintaining <10° C
  2. customconsumption of starting material
  3. additionThe reaction mixture was added slowly to saturated sodium bicarbonate in water (2300 mL)
  4. stirringto stir for 20 minutes
  5. customThe methylene chloride layer was separated
  6. extractionthe aqueous extracted twice with methylene chloride (2300 mL)
  7. concentrationconcentrated
  8. customThe residue was purified
  9. washby eluting through a silica gel (1 kg) plug with 50 to 100% ethyl acetate/hexane (hexane (6 L)+ethyl acetate (14 L)
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-6ded6625a729497c935bf6a71d61a800
Source dataset
uspto-grants-2014_08
Patent number
US08809356B2

Reaction notes

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