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

HRID 2175544Notes

Reaction equation

HRID 2175544 reaction equation
[CH2:1]([NH:3][CH:4]1[CH2:13][CH2:12][C:7]2([O:11][CH2:10][CH2:9][O:8]2)[CH2:6][CH2:5]1)[CH3:2].[CH2:14]([O:21][C:22](Cl)=[O:23])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C1COCC1>[CH2:1]([N:3]([CH:4]1[CH2:13][CH2:12][C:7]2([O:8][CH2:9][CH2:10][O:11]2)[CH2:6][CH2:5]1)[C:22](=[O:23])[O:21][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH3:2]

Participants

4

Reactant 2

HCID 10387Benzyl chloroformateHCID 15342646N-ethyl-1,4-dioxaspiro[4.5]decan-8-amine

Product 1

HCID 58562800Benzyl ethyl(1,4-dioxaspiro[4.5]decan-8-yl)carbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of N-ethyl-1,4-dioxaspiro[4.5]decan-8-amine (1.8 g, 9.9 mmol) from above step a in THF is treated with TEA (1.4, 9.9 mmol) and benzyloxycarbonyl chloride (1.4 mL, 9.9 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-0ef39a33bcd64fffb20a675d9e101a11
Source dataset
uspto-grants-2015_06
Patent number
US09062048B2

Reaction notes

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