Boron Trichloride → HCID 24962293, compound

HRID 2059563Notes

Reaction equation

HRID 2059563 reaction equation
[Cl:1][C:2]1[C:3]2[CH:10]=[CH:9][N:8]([C@H:11]3[C@:15]([C:17]#[CH:18])([OH:16])[C@H:14]([O:19]CC4C=CC(Cl)=CC=4Cl)[C@@H:13]([CH2:29][O:30]CC4C=CC(Cl)=CC=4Cl)[O:12]3)[C:4]=2[N:5]=[CH:6][N:7]=1.B(Cl)(Cl)Cl>C(Cl)Cl>[Cl:1][C:2]1[C:3]2[CH:10]=[CH:9][N:8]([C@H:11]3[C@:15]([C:17]#[CH:18])([OH:16])[C@H:14]([OH:19])[C@@H:13]([CH2:29][OH:30])[O:12]3)[C:4]=2[N:5]=[CH:6][N:7]=1

Participants

4

Reactant 2

HCID 25135Boron TrichlorideHCID 86642242HCID 86642242, compound

Product 1

HCID 24962293HCID 24962293, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a cold (−78° C.) solution of (2R,3R,4R,5R)-2-(4-Chloro-pyrrolo[2,3-d]pyrimidin-7-yl)-4-(2,4-dichlorobenzyloxy)-5-(2,4-dichlorobenzyloxymethyl)-3-ethynyl-tetrahydrofuran-3-ol I-5 (150 mg, 0.24 mmol, 1 equiv.) in dry DCM (20 ml) is added 1M solution of BCl3 in DCM (2.4 ml, 2.4 mmol, 10 equiv.) drop-wise and stirred at −78° C. for about 5 h. The reaction mixture is quenched with MeOH (15 mL) at 0° C. and stirred for 30 min. Solvent is evaporated and dried together with silica gel (4 ml), the crude product on silica gel is purified by flash chromatography (DCM:methanol=90:10) to give (2R,3R,4R,5R)-2-(4-Chloro-pyrrolo[2,3-d]pyrimidin-7-yl)-3-ethynyl-5-hydroxymethyl-tetrahydrofuran-3,4-diol I-6 as a brown foam.

Workup

  1. customThe reaction mixture is quenched with MeOH (15 mL) at 0° C.
  2. stirringstirred for 30 min
  3. customSolvent is evaporated
  4. customdried together with silica gel (4 ml)
  5. customthe crude product on silica gel is purified by flash chromatography (DCM:methanol=90:10)

Sources & evidence

ORD record
ord-7fbad02451844c3d8cf340b5f6373b54
Source dataset
uspto-grants-2012_10
Patent number
US08278282B2

Reaction notes

Loading…