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

HRID 354547

Reaction equation

HRID 354547 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-Butyloxycarbonyloxyimino-2-phenylacetonitrile (3.35 g, 13.6 mmoles) in dry tetrahydrofuran (40 ml) is slowly added with ice cooling to a stirred mixture of 1-fluoro-2-amino-4-pentene hydrochloride (1.9 g, 13.6 mmoles) and triethylamine (2.78 g, 27.2 mmoles) in tetrahydrofuran (30 ml). After standing overnight 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 stripped to give 1-fluoro-2-tert-butoxycarbonylamino-4-pentene (2.33 g, 85%) as an oil which is used 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

Sources & evidence

ORD record
ord-328d7ec2d5e34136ba793b896f94ba5d
Source dataset
uspto-grants-1983_03
Patent number
US04375477

Linked notes

Loading…