Propylamine → HCID 14988914, compound

HRID 481334Notes

Reaction equation

HRID 481334 reaction equation
[C:1]([CH2:4][O:5][CH:6]1[CH2:13][CH2:12][C:9]2([O:11][CH2:10]2)[CH:8]([C:14]2([CH3:22])[CH:16]([CH2:17][CH:18]=[C:19]([CH3:21])[CH3:20])[O:15]2)[CH:7]1[O:23][CH3:24])([OH:3])=O.C(N(CC)CC)C.C(C(Cl)=O)(C)(C)C.[CH2:39]([NH2:42])[CH2:40][CH3:41]>CN(C)C1C=CN=CC=1.ClCCl>[CH3:24][O:23][CH:7]1[CH:6]([O:5][CH2:4][C:1](=[O:3])[NH:42][CH2:39][CH2:40][CH3:41])[CH2:13][CH2:12][C:9]2([O:11][CH2:10]2)[CH:8]1[C:14]1([CH3:22])[CH:16]([CH2:17][CH:18]=[C:19]([CH3:21])[CH3:20])[O:15]1

Participants

7

Reactant 4

HCID 7852PropylamineHCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 14988880HCID 14988880, compound

Product 1

HCID 14988914HCID 14988914, compoundYield 75.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 6-carboxymethoxy-5-methoxy-4-[2-methyl-3-(3-methyl-2-butenyl)oxiranyl]-1-oxaspiro[2,5]-octane (9.0 mg), triethylamine (2.5 mg), and 4-dimethylaminopyridine (0.6 mg) in dichloromethane (1 ml) was added dropwise tert-butylcarbonyl chloride (3.5 mg) under ice cooling. The mixture was stirred for half an hour at ambient temperature and propylamine (2.9 mg) was added. After stirred for 2 hours at the same temperature, the solution was washed with water, aqueous HCl solution, saturated aqueous NaHCO3 solution, and brine successively. The organic layer was dried and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (diethyl ether-ethyl acetate =1-1) to give 5-methoxy-4-[2-methyl-3-(3-methyl-2-butenyl)oxiranyl]-6-propylcarbamoylmethoxy-1-oxaspiro[2,5]octane (7.6 mg).

Workup

  1. stirringAfter stirred for 2 hours at the same temperature
  2. washthe solution was washed with water, aqueous HCl solution, saturated aqueous NaHCO3 solution, and brine successively
  3. customThe organic layer was dried
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography on silica gel (diethyl ether-ethyl acetate =1-1)

Sources & evidence

ORD record
ord-7f204f1a661d4b3da04624cabd4702e2
Source dataset
uspto-grants-1998_08
Patent number
US05789405

Reaction notes

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