Diisopropylethylamine → HCID 58189203, compound

HRID 1423251Notes

Reaction equation

HRID 1423251 reaction equation
[CH2:1]([C@@H:8]1[NH:13][CH2:12][CH2:11][N:10]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)[CH:15]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[C:29](Cl)([O:31]C(=O)OC(Cl)(Cl)Cl)Cl.C(N(C(C)C)CC)(C)C.[NH:49]1[CH2:53][CH2:52][C@H:51]([OH:54])[CH2:50]1>C(Cl)Cl>[CH2:1]([C@H:8]1[CH2:9][N:10]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)[CH:15]=2)[CH2:11][CH2:12][N:13]1[C:29]([N:49]1[CH2:53][CH2:52][C@H:51]([OH:54])[CH2:50]1)=[O:31])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 81531Diisopropylethylamine2×HCID 94429TriphosgeneHCID 2733874(3S)-pyrrolidin-3-olHCID 16725642(S)-3-Benzyl-1-(3-cyclopentyloxy-4-methoxy-phenyl)-piperazine

Product 1

HCID 58189203HCID 58189203, compoundYield 64.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (S)-3-benzyl-1-(3-cyclopentyloxy-4-methoxy-phenyl)-piperazine (50 mg, 0.137 mmol) in CH2Cl2 (1 mL) at 0° C. was treated with triphosgene (25 mg, 0.084 mmol) followed by diisopropylethylamine (30 μL, 0.182 mmol). The reaction was allowed to warm to room temperature and stirred for 20 min then cooled to 0° C. and treated with an additional portion of diisopropylethylamine followed by pyrrolidin-3(S)-ol (30 μL, 0.37 mmol). The reaction mixture was allowed to warm to room temperature and stirred 16 h then quenched with MeOH, evaporated and purified by chromatography on silica gel using 5% MeOH/CH2Cl2 as eluant to afford the title compound as an oil (26 mg, 55%). LC/MS (Method B) 3.75 min, [M+1]+ 480.

Workup

  1. temperaturethen cooled to 0° C.
  2. temperatureto warm to room temperature
  3. stirringstirred 16 h
  4. customthen quenched with MeOH
  5. customevaporated
  6. custompurified by chromatography on silica gel using 5% MeOH/CH2Cl2 as eluant

Sources & evidence

ORD record
ord-c5e548e94ebb4fa2b7ebcdcc96eb7384
Source dataset
uspto-grants-2015_01
Patent number
US08927546B2

Reaction notes

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