Borane;tetrahydrofuran → HCID 58666872, compound

HRID 1354594Notes

Reaction equation

HRID 1354594 reaction equation
B1(C)OC(C2C=CC=CC=2)(C2C=CC=CC=2)[C@H]2N1CCC2.B.C1COCC1.[Cl:28][CH2:29][C:30]([C:32]1[CH:41]=[C:40]([Cl:42])[C:35]2[N:36]=[C:37]([CH3:39])[O:38][C:34]=2[CH:33]=1)=[O:31]>C1COCC1>[Cl:28][CH2:29][C@H:30]([C:32]1[CH:41]=[C:40]([Cl:42])[C:35]2[N:36]=[C:37]([CH3:39])[O:38][C:34]=2[CH:33]=1)[OH:31]

Participants

5

Reactant 3

HCID 2723981Borane;tetrahydrofuran2×HCID 2734713(3aS)-1-methyl-3,3-diphenyl-hexahydropyrrolo(1,2-c)(1,3,2)oxazaboroleHCID 22021526HCID 22021526, compound

Product 1

HCID 58666872HCID 58666872, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S)-Methyl-CBS-oxazaborolidine (1M in toluene, 0.745 mL, 0.745 mmol) and BH3-THF (8 mL, 8 mmol) is added at the same time a solution of BH3-THF (19 mL, 19 mmol) and a solution of 6-Chloroacetyl-4-chloro-2-methyl-benzooxazole (37.98 mmol) in 19 mL of THF. Both solutions are added dropwise over 30 minutes. The solution is stirred for 1 hour and quenched with the slow addition of methanol (50 mL). The solution is concentrated and the residue chromatographed over a short silica gel column (1:1 hexane/ethyl acetate).

Workup

  1. additionBoth solutions are added dropwise over 30 minutes
  2. customquenched with the slow addition of methanol (50 mL)
  3. concentrationThe solution is concentrated
  4. customthe residue chromatographed over a short silica gel column (1:1 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-47141d2430b8423da5fe2d51985ac318
Source dataset
uspto-grants-2007_05
Patent number
US07223757B2

Reaction notes

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