Triethylamine → tert-Butyl 4-(2-{[tert-butyldiphenylsilyl]oxy}ethyl)-4-hydroxy-1-piperidine-carboxylate

HRID 1663047Notes

Reaction equation

HRID 1663047 reaction equation
[Si:1](Cl)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:19][C:20]1([CH2:33][CH2:34][OH:35])[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:22][CH2:21]1.C(N(CC)CC)C.[Cl-].[NH4+]>ClCCl>[Si:1]([O:35][CH2:34][CH2:33][C:20]1([OH:19])[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:31])([CH3:30])[CH3:32])=[O:27])[CH2:22][CH2:21]1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 94078tert-ButyldiphenylchlorosilaneHCID 21936021Tert-butyl 4-hydroxy-4-(2-hydroxyethyl)piperidine-1-carboxylate

Product 1

HCID 21096980tert-Butyl 4-(2-{[tert-butyldiphenylsilyl]oxy}ethyl)-4-hydroxy-1-piperidine-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 21.50 ml (82.50 mmol) of tert-butyldiphenylsilyl chloride in 15 ml of dichloromethane is added dropwise, under an inert atmosphere, to a solution of 18.4 g (75 mmol) of tert-butyl 4-hydroxy-4-(2-hydroxyethyl)-1-piperidinecarboxylate, obtained in step 12.1, and 11.60 ml (82.50 mmol) of triethylamine in 100 ml of dichloromethane, cooled to about 0° C. The mixture is allowed to warm to room temperature and stifling is then continued for 12 hours. Saturated aqueous ammonium chloride solution is added to the reaction medium. The aqueous phase is separated out and extracted twice with dichloromethane, the combined organic phases are washed with saturated aqueous sodium chloride solution and dried over sodium sulfate, and the filtrate is concentrated under reduced pressure. The residue thus obtained is purified by chromatography on silica gel, eluting with a 10/90 and then 20/80 mixture of ethyl acetate and cyclohexane.

Workup

  1. temperatureto warm to room temperature
  2. customThe aqueous phase is separated out
  3. extractionextracted twice with dichloromethane
  4. washthe combined organic phases are washed with saturated aqueous sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. concentrationthe filtrate is concentrated under reduced pressure
  7. customThe residue thus obtained
  8. customis purified by chromatography on silica gel
  9. washeluting with a 10/90
  10. addition20/80 mixture of ethyl acetate and cyclohexane

Sources & evidence

ORD record
ord-48086358f1794d09be2a7ef296345d39
Source dataset
uspto-grants-2011_10
Patent number
US08034818B2

Reaction notes

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