Octyl isocyanate → 3-[1-Phenylmethyl-2-pyrrolidinyl]phenyl octylcarbamate

HRID 1742267Notes

Reaction equation

HRID 1742267 reaction equation
[C:1]1([CH2:7][N:8]2[CH2:12][CH2:11][CH2:10][CH:9]2[C:13]2[CH:14]=[C:15]([OH:19])[CH:16]=[CH:17][CH:18]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:20]([N:28]=[C:29]=[O:30])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]>O1CCCC1>[CH2:20]([NH:28][C:29](=[O:30])[O:19][C:15]1[CH:16]=[CH:17][CH:18]=[C:13]([CH:9]2[CH2:10][CH2:11][CH2:12][N:8]2[CH2:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:14]=1)[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]

Participants

4

Reactant 2

HCID 76616Octyl isocyanateHCID 233612863-(1-Phenylmethyl-2-pyrrolidinyl)phenol

Product 1

HCID 152913763-[1-Phenylmethyl-2-pyrrolidinyl]phenyl octylcarbamateYield 52%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(1-phenylmethyl-2-pyrrolidinyl)phenol (0.06 g) in dry tetrahydrofuran (30 ml) was added octyl isocyanate (0.44 ml) at ambient temperature, under nitrogen. The reaction mixture was stirred for 17 hrs and filtered through a pad of celite. The filter cake was washed with ethyl acetate and the combined filtrates were concentrated. The residue was purified by flash column chromatography (silica gel, dichloromethane). The appropriate fractions were collected and concentrated to give 0.50 g (52%) of product. The analytical sample was prepared by flushing the product through alumina with ether.

Workup

  1. filtrationfiltered through a pad of celite
  2. washThe filter cake was washed with ethyl acetate
  3. concentrationthe combined filtrates were concentrated
  4. customThe residue was purified by flash column chromatography (silica gel, dichloromethane)
  5. customThe appropriate fractions were collected
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-8cbd23344ba04621847389253831e1e2
Source dataset
uspto-grants-1994_08
Patent number
US05338739

Reaction notes

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