Trityl chloride → (1S,4R)-methyl 4-(tritylamino)cyclopent-2-enecarboxylate

HRID 1427327Notes

Reaction equation

HRID 1427327 reaction equation
Cl.[CH3:2][O:3][C:4]([C@H:6]1[CH2:10][C@@H:9]([NH2:11])[CH:8]=[CH:7]1)=[O:5].[C:12]1([C:18](Cl)([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(CC)CC)C>C(Cl)Cl>[C:18]([NH:11][C@@H:9]1[CH2:10][C@H:6]([C:4]([O:3][CH3:2])=[O:5])[CH:7]=[CH:8]1)([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 60152708(1S,4R)-Methyl 4-aminocyclopent-2-enecarboxylate hydrochloride

Product 1

HCID 78358250(1S,4R)-methyl 4-(tritylamino)cyclopent-2-enecarboxylateYield 105.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Methyl-(1S,4R)-4-aminocyclopent-2-ene-1-carboxylate hydrochloride (5.50 g) was suspended in methylene chloride (60 mL), to which triphenylmethyl chloride (9.06 g, 0.0325 mol) was added. The mixture was then cooled to 0° C. Triethylamine (10.8 mL, 0.0774 mol) was then added dropwise keeping the temperature less than 10° C. Upon completion of addition, the mixture was allowed to warm to 20-25° C. The mixture was left to stir at 20-25° C. for 17 hours. The mixture was then washed with water (3×50 mL). The aqueous washes were combined and extracted with DCM (50 mL). The organics were combined and washed with brine (20 mL) and the solvent was removed under reduced pressure to afford the title compound as a brown oil (12.5 g) which was used without further purification. 1H NMR (300 MHz, CDCl3, δ): 7.58 (m, 6H), 7.27 (m, 6H), 7.18 (m, 3H), 5.57 (m, 1H), 4.93 (m, 1H), 3.76 (m, 1H), 3.65 (s, 3H), 3.18 (m, 1H), 2.11 (m, 1H), 1.90 (m, 1H) and 1.53 (m, 1H).

Workup

  1. additionwas added
  2. customthe temperature less than 10° C
  3. additionUpon completion of addition
  4. temperatureto warm to 20-25° C
  5. waitThe mixture was left
  6. washThe mixture was then washed with water (3×50 mL)
  7. extractionextracted with DCM (50 mL)
  8. washwashed with brine (20 mL)
  9. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-04a818ab8fb248c3a579114a08304c4a
Source dataset
uspto-grants-2015_01
Patent number
US08933225B2

Reaction notes

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