Pyridine → HCID 66918652, compound

HRID 1367508Notes

Reaction equation

HRID 1367508 reaction equation
[C:1]([Si:5]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[O:6][C@@H:7]1[CH2:11][C@@H:10](O)[C@@H:9]([O:13][CH:14]([CH3:16])[CH3:15])[CH2:8]1)([CH3:4])([CH3:3])[CH3:2].[N:29]1C=CC=C[CH:30]=1.FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O>C(Cl)Cl>[C:1]([Si:5]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[O:6][C@@H:7]1[CH2:11][C@H:10]([C:30]#[N:29])[C@@H:9]([O:13][CH:14]([CH3:15])[CH3:16])[CH2:8]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 1049PyridineHCID 67749Trifluoromethanesulfonic anhydrideHCID 66918897HCID 66918897, compound

Product 1

HCID 66918652HCID 66918652, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-35 °C

Procedure

(1S,2R,4S) and (1R,2S,4R)-4-(tert-Butyl-diphenyl-silanyloxy)-2-isopropoxy-cyclopentanol (510 mg, 1.28 mmol) was dissolved in DCM (12 ml) and pyridine was added (206 μl, 2.56 mmol). The mixture was cooled to −35° C. and a solution of trifluoromethanesulfonic anhydride (253 μl, 1.54 mmol) in DCM (3 ml) was added. After the reaction mixture had been stirred for 5 h at −20° C. it was concentrated and passed trough a short plug of silica gel and then evaporated to dryness. The remaining oil was dissolved in THF (12 ml) and a solution of tertrabutylammonium cyanide in THF (3 ml) was added dropwise at −45° C. The reaction mixture was stirred at room temperature over night and then evaporated. The remaining yellow oil was purified by silica column chromatography (heptane/EtOAc 9:1) to obtain the title compound (311 mg, 60%) as colorless oil. MS (EI): 408.4 (M+H)+.

Workup

  1. concentrationwas concentrated
  2. customevaporated to dryness
  3. dissolutionThe remaining oil was dissolved in THF (12 ml)
  4. additiona solution of tertrabutylammonium cyanide in THF (3 ml) was added dropwise at −45° C
  5. stirringThe reaction mixture was stirred at room temperature over night
  6. customevaporated
  7. customThe remaining yellow oil was purified by silica column chromatography (heptane/EtOAc 9:1)

Sources & evidence

ORD record
ord-139349225bf246b2b09249cdf023374a
Source dataset
uspto-grants-2011_02
Patent number
US07893099B2

Reaction notes

Loading…