Sodium Bicarbonate → HCID 15386083, compound

HRID 1109632Notes

Reaction equation

HRID 1109632 reaction equation
[C:1]([CH:6]1[CH2:11][CH:10]([CH2:12][O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])[CH2:9][NH:8][C:7]1=[O:21])([O:3][CH2:4][CH3:5])=[O:2].F[B-](F)(F)F.[CH3:27][O+](C)C.C(=O)(O)[O-].[Na+]>ClCCl>[CH3:27][O:21][C:7]1[CH:6]([C:1]([O:3][CH2:4][CH3:5])=[O:2])[CH2:11][CH:10]([CH2:12][O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])[CH2:9][N:8]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 2735153Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1)HCID 15386082HCID 15386082, compound

Product 1

HCID 15386083HCID 15386083, compoundYield 88.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
4 °C

Procedure

To a solution of 14.9 g 3-carboethoxy-5-[t-butyl(dimethyl)silyloxymethyl]-2-piperidone in 400 ml anhydrous dichloromethane at 4° C. were added 7.7 g of trimethyloxonium tetrafluoroborate. The mixture was first stirred for 90 minutes at 4° C. and then for 1 hour at 22° C. The resulting solution was poured into a saturated solution of sodium bicarbonate and extracted with three portions of dichloromethane. The combined organic extracts were washed with water and brine, dried over magnesium sulfate and evaporated to give 13.8 g of the title compound: 300-MHz 1H NMR (CDCl3) δ0.04 (s, 6H), 0.88 (s, 9H), 1.25 (t, J=7 Hz, 3H), 1.51-2.18 (m, 3H), 3.11-3.32 (m, 2H), 3.48-3.56 (m, 2H), 3.60-3.76 (m, 4H), 4.19 (t, J=7 Hz, 2H).

Workup

  1. waitfor 1 hour at 22° C
  2. extractionextracted with three portions of dichloromethane
  3. washThe combined organic extracts were washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-f5c8a394c7e840ff85d76e89820313e2
Source dataset
uspto-grants-1994_06
Patent number
US05321150

Reaction notes

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