Diisopropylethylamine → HCID 86612297, compound

HRID 2074430Notes

Reaction equation

HRID 2074430 reaction equation
C[O:2][C:3]1[C:12]([CH3:13])=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][C@@H:6]([CH:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1)[O:7][C@H:8]2[CH2:14][NH:15][CH:16]=[O:17].Br[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33].C(N(C(C)C)CC)(C)C>C(#N)C>[CH2:35]([O:34][C:32](=[O:33])[CH:31]([N:21]1[CH2:20][CH2:19][CH:18]([C@@H:6]2[CH2:5][C:4]3[C:9](=[CH:10][CH:11]=[C:12]([CH3:13])[C:3]=3[OH:2])[C@H:8]([CH2:14][NH:15][CH:16]=[O:17])[O:7]2)[CH2:23][CH2:22]1)[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:25]=1)[CH3:36]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 2780092Ethyl 2-(2-bromophenyl)acetateHCID 11695413HCID 11695413, compound

Product 1

HCID 86612297HCID 86612297, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Stir a solution of N-((1R,3S)-5-methoxy-6-methyl-3-(4-piperidinyl)-1-isochromanyl-methyl)formamide (200 mg, 0.58 mmole), ethyl 2-bromophenylacetate (229 mg, 0.94 mmole) and diisopropylethylamine (243 mg, 1.88 mmole) in acetonitrile overnight at room temperature. Add ethyl acetate and water (2 mL each), then separate the organic phase and dry over Na2SO4. Purify the crude product on a 4 g silica gel column (eluting with ethyl acetate:heptane 3:1). Collect the appropriate fractions and concentrate to obtain the title compound. It was used without further purification in the next step.

Workup

  1. customAdd ethyl acetate and water (2 mL each), then separate the organic phase
  2. dry with materialdry over Na2SO4
  3. customPurify the crude product
  4. washon a 4 g silica gel column (eluting with ethyl acetate:heptane 3:1)
  5. customCollect the appropriate fractions
  6. concentrationconcentrate

Sources & evidence

ORD record
ord-91279cedad6b4d69ac7ee744a0ad91f7
Source dataset
uspto-grants-2011_04
Patent number
US07919508B2

Reaction notes

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