Water → N-Boc-1-fluoropent-4-EN-2-amine

HRID 223319

Reaction equation

HRID 223319 reaction equation
[C:1]([O:5][C:6]([O:8]N=C(C1C=CC=CC=1)C#N)=O)([CH3:4])([CH3:3])[CH3:2].Cl.[F:20][CH2:21][CH:22]([NH2:26])[CH2:23][CH:24]=[CH2:25].C(N(CC)CC)C.O>O1CCCC1>[F:20][CH2:21][CH:22]([NH:26][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:8])[CH2:23][CH:24]=[CH2:25]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 938652-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrileHCID 205083291-Fluoropent-4-EN-2-amine hcl

Product 1

HCID 20508337N-Boc-1-fluoropent-4-EN-2-amineYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Tert-Butoxycarbonyloxyimino-2-phenylacetonitrile (3.34 g, 13.6 mmoles) in dry tetrahydrofuran (40 ml) is slowly added with ice cooling to a stirred mixture of 1-fluoro-2-amino-4pentene hydrochloride (1.9 g, 13.6 mmoles) prepared in Example 2 and triethylamine (2.78 g, 27.2 mmoles) in tetrahydrofuran (30 ml). After standing overnight (about 16 hours) at room temperature, water is added, the tetrahydrofuran is removed under reduced pressure, and the residue is extracted twice with ether. After washing with 1 N sodium hydroxide, then with water until neutral, the organic layer is dried and concentrated at reduced pressure to give 1-fluoro-2-tert-butoxycarbonylamino-4-pentene (2.33 g, 85%) as an oil which is used in Example 4 without further purification.

Workup

  1. customthe tetrahydrofuran is removed under reduced pressure
  2. extractionthe residue is extracted twice with ether
  3. washAfter washing with 1 N sodium hydroxide
  4. dry with materialwith water until neutral, the organic layer is dried
  5. concentrationconcentrated at reduced pressure

Sources & evidence

ORD record
ord-19fabd3244a94c2db74dc639067bb9fb
Source dataset
uspto-grants-1982_10
Patent number
US04353828

Linked notes

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