Triethylamine → 2,3-dihydro-5-(3',4'-dichlorophenyl)-6,7-bis(hydroxymethyl)-1H-pyrrolizine Bis(isopropylcarbamate)

HRID 569792Notes

Reaction equation

HRID 569792 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[N:10]3[C:14](=[C:15]([CH2:19][OH:20])[C:16]=2[CH2:17][OH:18])[CH2:13][CH2:12][CH2:11]3)[CH:5]=[CH:6][C:7]=1[Cl:8].C(N(CC)CC)C.[CH:28]([N:31]=[C:32]=[O:33])([CH3:30])[CH3:29]>ClCCl>[CH:28]([NH:31][C:32](=[O:18])[OH:33])([CH3:30])[CH3:29].[CH:28]([NH:31][C:32](=[O:18])[OH:33])([CH3:30])[CH3:29].[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[N:10]3[C:14](=[C:15]([CH2:19][OH:20])[C:16]=2[CH2:17][OH:18])[CH2:13][CH2:12][CH2:11]3)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 61277Isopropyl isocyanateHCID 320364[5-(3,4-Dichlorophenyl)-2,3-dihydro-1H-pyrrolizine-6,7-diyl]dimethanol

Product 1

HCID 867420682,3-dihydro-5-(3',4'-dichlorophenyl)-6,7-bis(hydroxymethyl)-1H-pyrrolizine Bis(isopropylcarbamate)Yield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2,3-dihydro-5-(3',4'-dichlorophenyl)-6,7-bis(hydroxymethyl)-1H-pyrrolizine (6.244 g, 0.02 mol) and triethylamine (0.5 mL) in dichloromethane (45 mL) was treated with isopropyl isocyanate (7 mL, ca. 10 equiv) and refluxed for 1.5 h. The mixture was concentrated to dryness in vacuo and the off-white residue was crystallized from ethyl acetate-isopropyl ether to give about an 81% yield of 2,3-dihydro-5-(3',4'-dichlorophenyl)-6,7-bis(hydroxymethyl)-1H-pyrrolizine Bis(isopropylcarbamate).

Workup

  1. temperaturerefluxed for 1.5 h
  2. concentrationThe mixture was concentrated to dryness in vacuo
  3. customthe off-white residue was crystallized from ethyl acetate-isopropyl ether

Sources & evidence

ORD record
ord-29e8bc9a5a2241c9a9a19b1bd6ffa008
Source dataset
uspto-grants-1988_03
Patent number
US04734423

Reaction notes

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