Diisopropylethylamine → 1-{[3-(3-Chloro-4-methoxyphenyl)isoxazol-4-yl]carbonyl}-5-methyl-3-phenylpyrrolidin-3-ol

HRID 1446352Notes

Reaction equation

HRID 1446352 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:10]2[C:14]([C:15]([OH:17])=O)=[CH:13][O:12][N:11]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].C(N(C(C)C)C(C)C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[CH3:49][CH:50]1[NH:54][CH2:53][C:52]([C:56]2[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=2)([OH:55])[CH2:51]1>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:10]2[C:14]([C:15]([N:54]3[CH:50]([CH3:49])[CH2:51][C:52]([C:56]4[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=4)([OH:55])[CH2:53]3)=[O:17])=[CH:13][O:12][N:11]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 30513955-Methyl-3-phenyl-pyrrolidin-3-olHCID 591701453-(3-Chloro-4-methoxyphenyl)-isoxazole-4-carboxylic acid

Product 1

HCID 591702091-{[3-(3-Chloro-4-methoxyphenyl)isoxazol-4-yl]carbonyl}-5-methyl-3-phenylpyrrolidin-3-olYield 72.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3-(3-chloro-4-methoxyphenyl)-isoxazole-4-carboxylic acid (10 mg, 0.04 mmol), N-ethyl-N-isopropylpropan-2-amine (14 μL, 0.08 mmol, 2 equ.) and TBTU (15 mg, 0.046 mmol, 1.2 equ.) in DMF (0.3 mL) was added to 5-methyl-3-phenylpyrrolidin-3-ol (7 mg, 0.04 mmol). After 1 h at rt the crude product was purified by RP-HPLC, evaporated and dried in vacuum to yield the title compound (12 mg). MS (ESI, pos. ion) m/z: calcd for C22H21ClN2O4: 412.1190, found 412.1189.

Workup

  1. customAfter 1 h at rt the crude product was purified by RP-HPLC
  2. customevaporated
  3. customdried in vacuum

Sources & evidence

ORD record
ord-e3eb017b4fc04e3bb6f5f06fb2d8706a
Source dataset
uspto-grants-2010_02
Patent number
US07666888B2

Reaction notes

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