Benzyl Alcohol → HCID 22804043, compound

HRID 2049467Notes

Reaction equation

HRID 2049467 reaction equation
C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:8])C=CC=CC=1.[CH2:18]([N:20]([CH2:23]C)[CH2:21][CH3:22])C.[CH2:25]([OH:32])[C:26]1[CH:31]=[CH:30]C=CC=1>C1C=CC=CC=1>[CH3:23][N:20]([CH3:18])[C@H:21]1[CH2:22][CH2:30][CH2:31][C@H:26]1[C:25]([OH:32])=[O:8]

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azide

Product 1

HCID 22804043HCID 22804043, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

A solution of diphenyl phosphoryl azide (44.3 g., 0.16 mole) in 50 ml. benzene was added in 15 minutes to a solution of the part B amino acid (25.3 g., 0.16 mole) in 750 ml. benzene. After 15 minutes, triethyl amine (16.2 g., 0.16 mole) was added over 5 minutes. The solution was stirred for 30 minutes, then refluxed for 30 minutes. Benzyl alcohol (51.8 g., 0.48 mole) was added and the mixture refluxed overnight. The solution was extracted with 10% HCl. The aqueous layer was washed with ether, made basic with 40% NaOH, and extracted with ether. The ether layer was washed with water and saturated salt solution, dried (MgSO4), and evaporated to a brown oil (7.9 g.). The nmr (CDCl3) of the crude product was reasonable for a benzyl carbamate. The benzyl N-[2-(dimethylamino)cyclopentyl]carbamate material was used without purification.

Workup

  1. temperaturerefluxed for 30 minutes
  2. temperaturethe mixture refluxed overnight
  3. extractionThe solution was extracted with 10% HCl
  4. washThe aqueous layer was washed with ether
  5. extractionextracted with ether
  6. washThe ether layer was washed with water and saturated salt solution
  7. dry with materialdried (MgSO4)
  8. customevaporated to a brown oil (7.9 g.)
  9. customThe benzyl N-[2-(dimethylamino)cyclopentyl]carbamate material was used without purification

Sources & evidence

ORD record
ord-dc5fbc6138624c4bb29fe3e126ef636a
Source dataset
uspto-grants-1980_04
Patent number
US04197308

Reaction notes

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