Triethylborane → 2-[(4aS,6R,7aS)-2-(4-methoxyphenyl)-hexahydrocyclopenta[d][1,3]dioxin-6-yl]-1H-isoindole-1,3(2H)-dione

HRID 1677929Notes

Reaction equation

HRID 1677929 reaction equation
C(=S)(OC1C=CC=CC=1)O[C@@H:3]1[C@@H:7]2[O:8][CH:9]([C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=3)[O:10][CH2:11][C@@H:6]2[CH2:5][C@H:4]1[N:20]1[C:28](=[O:29])[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:21]1=[O:30].C[Si]([SiH]([Si](C)(C)C)[Si](C)(C)C)(C)C.C(B(CC)CC)C.CCCCCC>C1(C)C=CC=CC=1>[CH3:19][O:18][C:15]1[CH:16]=[CH:17][C:12]([CH:9]2[O:8][C@H:7]3[CH2:3][C@H:4]([N:20]4[C:28](=[O:29])[C:27]5[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=5)[C:21]4=[O:30])[CH2:5][C@H:6]3[CH2:11][O:10]2)=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 7357Triethylborane2×HCID 8058Hexane2×HCID 123134Tris(trimethylsilyl)silane2×HCID 59671288O-[(4aS,6R,7S,7aR)-6-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-2-(4-methoxyphenyl)hexahydrocyclopenta[d][1,3]dioxin-7-yl] O-phenyl thiocarbonate

Product 1

HCID 596714242-[(4aS,6R,7aS)-2-(4-methoxyphenyl)-hexahydrocyclopenta[d][1,3]dioxin-6-yl]-1H-isoindole-1,3(2H)-dioneYield 42%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of O-[(4aS,6R,7S,7aR)-6-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-2-(4-methoxyphenyl)hexahydrocyclopenta[d][1,3]dioxin-7-yl] O-phenyl thiocarbonate (56.9 mg, 0.107 mmol) in toluene (4.00 mL) was added tris(trimethylsilyl)silane (0.0700 mL, 0.227 mmol). Air (2.00 mL) was bubbled through the solution and a 1.00 M solution of triethylborane in hexane (0.0320 mL, 0.0320 mmol) was added and the reaction was stirred for 2 h. More tris(trimethylsilyl)silane (0.0700 mL, 0.227 mmol) and 1.00 M triethylborane in hexane (0.0300 mL, 0.0300 mmol) were added, and the mixture was stirred another 6 h. The mixture was then concentrated in vacuo and the residue was purified via silica gel chromatography eluting with a gradient of 0 to 20% EtOAc in DCM to afford the title compound (16.9 mg, 42%). LC/MS: Rt=2.03 min, ES+ 380. (AA standard).

Workup

  1. customAir (2.00 mL) was bubbled through the solution
  2. stirringthe mixture was stirred another 6 h
  3. concentrationThe mixture was then concentrated in vacuo
  4. customthe residue was purified via silica gel chromatography
  5. washeluting with a gradient of 0 to 20% EtOAc in DCM

Sources & evidence

ORD record
ord-9ac43fdff1904e9bb5a7ad6f28e6e8e0
Source dataset
uspto-grants-2011_08
Patent number
US08008307B2

Reaction notes

Loading…