4-Chloro-1-butanol → HCID 68591650, compound

HRID 1776970Notes

Reaction equation

HRID 1776970 reaction equation
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([N:18]3[C@H:22]([C:23]([OH:25])=[O:24])[CH2:21][C@@H:20]4[CH2:26][CH2:27][CH2:28][C@H:19]34)=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[Cl:29][CH2:30][CH2:31][CH2:32][CH2:33]O.Cl.C(N=C=NCCCN(C)C)C>C(Cl)Cl>[N:18]1([C:16]([O:15][CH2:14][CH:12]2[C:13]3[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=3[C:6]3[C:11]2=[CH:10][CH:9]=[CH:8][CH:7]=3)=[O:17])[C@H:22]([C:23]([O:25][CH2:33][CH2:32][CH2:31][CH2:30][Cl:29])=[O:24])[CH2:21][C@@H:20]2[CH2:26][CH2:27][CH2:28][C@H:19]12

Participants

5

Reactant 3

HCID 135694-Chloro-1-butanolHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 685904191-(9H-Fluoren-9-ylmethyl) (2S,3aS,6aS)-hexahydrocyclopenta[b]pyrrole-1,2(2H)-dicarboxylate

Product 1

HCID 68591650HCID 68591650, compoundYield 45.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

(2S,3aS,6aS)-1-(((9H-fluoren-9-yl)methoxy)carbonyl)octahydrocyclopenta[b]pyrrole-2-carboxylic acid (0.250 g, 0.66 mmol) and 4-chloro-1-butanol (0.1 ml, 0.99 mmol) were dissolved under nitrogen in CH2Cl2 (5 ml) and the mixture was cooled to 0° C. N-ethyl-N′-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDC) (0.190 g, 0.99 mmol) and N,N-dimethylaminopyridine (DMAP) (0.016 g, 0.13 mmol) were added and the reaction was slowly warmed to room temperature and stirred for 4 h. Then the mixture was diluted with CH2Cl2 (10 ml) and washed with 5% aqueous NaHCO3, 5% aqueous Na2HPO4 and brine. The organic layer was dried over sodium sulphate, concentrated under reduced pressure and purified by flash chromatography (n-hexane/EtOAc 80:20 as eluent) affording the title compound as an oil (0.14 g, 45%)

Workup

  1. temperaturethe reaction was slowly warmed to room temperature
  2. washwashed with 5% aqueous NaHCO3, 5% aqueous Na2HPO4 and brine
  3. dry with materialThe organic layer was dried over sodium sulphate
  4. concentrationconcentrated under reduced pressure
  5. custompurified by flash chromatography (n-hexane/EtOAc 80:20 as eluent)

Sources & evidence

ORD record
ord-d3794a66b79d486486f2f090460aaf7e
Source dataset
uspto-grants-2016_02
Patent number
US09266820B2

Reaction notes

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