Chloroform → (3RS,4RS)-4-(3-aminopropyl)-7-methoxymethoxy-3-(4-methoxymethoxyphenyl)-3-methylchroman

HRID 1792335Notes

Reaction equation

HRID 1792335 reaction equation
[N:1]([CH2:4][CH2:5][CH2:6][CH:7]1[C:16]2[C:11](=[CH:12][C:13]([O:17][CH2:18][O:19][CH3:20])=[CH:14][CH:15]=2)[O:10][CH2:9][C:8]1([C:22]1[CH:27]=[CH:26][C:25]([O:28][CH2:29][O:30][CH3:31])=[CH:24][CH:23]=1)[CH3:21])=[N+]=[N-].C(Cl)(Cl)Cl.O.N>CO.O1CCCC1.[Pd]>[NH2:1][CH2:4][CH2:5][CH2:6][CH:7]1[C:16]2[C:11](=[CH:12][C:13]([O:17][CH2:18][O:19][CH3:20])=[CH:14][CH:15]=2)[O:10][CH2:9][C:8]1([C:22]1[CH:23]=[CH:24][C:25]([O:28][CH2:29][O:30][CH3:31])=[CH:26][CH:27]=1)[CH3:21]

Participants

7

Reactant 3

HCID 6212ChloroformHCID 12896473Azane;hydrateHCID 22033112HCID 22033112, compound

Product 1

HCID 22033411(3RS,4RS)-4-(3-aminopropyl)-7-methoxymethoxy-3-(4-methoxymethoxyphenyl)-3-methylchromanYield 73%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

(3RS,4RS)-4-(3-Azidopropyl}7-methoxymethoxy-3-(4-methoxymethoxyphenyl)-3-methylchroman (170 mg, 4.0 mmol) was dissolved in methanol (20 ml) and tetrahydrofuran (5 ml), 10% palladium on carbon (50 mg) was added to this solution, which was then stirred at room temperature under hydrogen for 12 hours. The reaction solution was filtered through cellite and concentrated under reduced pressure to give a crude product. This crude product thus obtained was subjected to silica gel column chromatography (chloroform:methanol:ammonia water=10:1:0.1) to give (3RS,4RS)-4-(3-aminopropyl)-7-methoxymethoxy-3-(4-methoxymethoxyphenyl)-3-methylchroman (116 mg, yield 73%).

Workup

  1. filtrationThe reaction solution was filtered through cellite
  2. concentrationconcentrated under reduced pressure
  3. customto give a crude product
  4. customThis crude product thus obtained

Sources & evidence

ORD record
ord-2f18d5d1774d4e6f87311fe846750064
Source dataset
uspto-grants-2006_07
Patent number
US07074819B2

Reaction notes

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