Trityl chloride → Tert-butyl 4-[3-(tert-butoxy)-2-hydroxypropyl]-4-hydroxy-1-piperidinecarboxylate

HRID 47324Notes

Reaction equation

HRID 47324 reaction equation
[OH:1][CH:2]([CH2:18][OH:19])[CH2:3][C:4]1([OH:17])[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1.Cl[C:21]([C:34]1C=CC=CC=1)([C:28]1C=CC=CC=1)[C:22]1C=CC=CC=1>N1C=CC=CC=1>[C:21]([O:19][CH2:18][CH:2]([OH:1])[CH2:3][C:4]1([OH:17])[CH2:5][CH2:6][N:7]([C:10]([O:12][C:13]([CH3:14])([CH3:15])[CH3:16])=[O:11])[CH2:8][CH2:9]1)([CH3:34])([CH3:28])[CH3:22]

Participants

4

Reactant 2

HCID 6456Trityl chlorideHCID 22744545Tert-butyl 4-(2,3-dihydroxypropyl)-4-hydroxy-1-piperidinecarboxylate

Product 1

HCID 22744586Tert-butyl 4-[3-(tert-butoxy)-2-hydroxypropyl]-4-hydroxy-1-piperidinecarboxylateYield 93.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

9.11 g of tert-butyl 4-(2,3-dihydroxypropyl)-4-hydroxy-1-piperidinecarboxylate was dissolved in 40 ml pyridine, 10.0 g of chlorotriphenylmethane was added thereto, and the mixture was stirred at room temperature overnight. The reaction solution was partitioned into ethyl acetate and water, washed with 2 N hydrochloric acid, water, saturated aqueous sodium bicarbonate and brine, and dried over magnesium sulfate. After filtration, the solvent was evaporated, and the resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give 10.3 g of tert-butyl 4-[3-(tert-butoxy)-2-hydroxypropyl]-4-hydroxy-1-piperidinecarboxylate.

Workup

  1. customThe reaction solution was partitioned into ethyl acetate and water
  2. washwashed with 2 N hydrochloric acid, water, saturated aqueous sodium bicarbonate and brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationAfter filtration
  5. customthe solvent was evaporated
  6. customthe resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-e9eadd2fa35b437b8d5d983f848468fb
Source dataset
uspto-grants-2004_03
Patent number
US06699870B2

Reaction notes

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