Triethylamine → HCID 117629272, compound

HRID 878408Notes

Reaction equation

HRID 878408 reaction equation
[CH2:1]([N:4]([CH2:11][CH:12]=[CH2:13])[C@@H:5]1[CH2:9][O:8][CH2:7][C@H:6]1O)[CH:2]=[CH2:3].C([N:16](CC)CC)C.CS(Cl)(=O)=O.[OH-].[NH4+]>C(OC)(C)(C)C>[CH2:1]([N:4]([CH2:11][CH:12]=[CH2:13])[C@H:5]1[C@H:6]([NH2:16])[CH2:7][O:8][CH2:9]1)[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 8471Triethylamine2×HCID 14923Ammonium HydroxideHCID 31297Methanesulfonyl chlorideHCID 117629641HCID 117629641, compound

Product 1

HCID 117629272HCID 117629272, compound

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

To a solution of trans-4-(diprop-2-en-1-ylamino)tetrahydrofuran-3-ol (50.0 g, 0.273 mol) in methyl tert-butyl ether was added triethylamine (44.0 g, 0.437 mol) at 5° C. Methanesulfonyl chloride (25.4 mL, 0.327 mol) was added using an addition funnel over a period of 15 min at 5° C. After 30 minutes, triethylamine (55.0 g, 0.546 mol) was added and the reaction was allowed to warm to ambient temperature. Ammonium hydroxide (29% aqueous solution, 700 mL) was then added. After 16 hours, the organic layer was separated, and the aqueous layer was washed with methyl tert-butyl ether (3×250 mL). The organic layers were combined, washed with brine, dried over sodium sulfate, and concentrated under reduced pressure to afford adduct trans-N,N-di(prop-2-en-1-yl)tetrahydrofuran-3,4-diamine. The material was used without further purification.

Workup

  1. customof 15 min
  2. customat 5° C
  3. waitAfter 16 hours
  4. customthe organic layer was separated
  5. washthe aqueous layer was washed with methyl tert-butyl ether (3×250 mL)
  6. washwashed with brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e6a71551d462464cb0a6c59c323d50b1
Source dataset
uspto-grants-2015_03
Patent number
US08987456B2

Reaction notes

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