Benzyl chloroformate → Benzyl propyl(1,4-dioxaspiro[4.5]decan-8-yl)carbamate

HRID 1896864Notes

Reaction equation

HRID 1896864 reaction equation
[CH2:1]([NH:4][CH:5]1[CH2:14][CH2:13][C:8]2([O:12][CH2:11][CH2:10][O:9]2)[CH2:7][CH2:6]1)[CH2:2][CH3:3].[CH2:15]([O:22][C:23](Cl)=[O:24])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C1COCC1>[CH2:1]([N:4]([CH:5]1[CH2:6][CH2:7][C:8]2([O:12][CH2:11][CH2:10][O:9]2)[CH2:13][CH2:14]1)[C:23](=[O:24])[O:22][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:2][CH3:3]

Participants

4

Reactant 2

HCID 10387Benzyl chloroformateHCID 118200814-n-Propylamino-cyclohexanone-ethyleneketal

Product 1

HCID 58562547Benzyl propyl(1,4-dioxaspiro[4.5]decan-8-yl)carbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of N-propyl-1,4-dioxaspiro[4.5]decan-8-amine (2.97 g, 14.9 mmol) from above step A in THF is treated with TEA (2.1, 14.9 mmol) and benzyloxycarbonyl chloride (2.1 mL, 14.9 mmol). The mixture was stirred for 18 h at room temperature. THF was removed under vacuum and the residue was taken EtOAc and washed with 10% citric acid, saturated NaHCO3, and saturated NaCl. The solution was dried over Na2SO4 and evaporated under vacuum. The residue was purified by silica column chromatography to give the title compound.

Workup

  1. customTHF was removed under vacuum
  2. washwashed with 10% citric acid, saturated NaHCO3, and saturated NaCl
  3. dry with materialThe solution was dried over Na2SO4
  4. customevaporated under vacuum
  5. customThe residue was purified by silica column chromatography

Sources & evidence

ORD record
ord-bc61a970371a44dbb50ff4f3fd9c3ec4
Source dataset
uspto-grants-2013_08
Patent number
US08518969B2

Reaction notes

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