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Triethylamine → [(2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-[3-[[4-[(E)-4-hydroxybut-1-enyl]phenyl]methyl]-4-methyl-indol-1-yl]tetrahydropyran-2-yl]methyl acetate

HRID 2284527
Notes
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Reaction equation

HRID 2284527 reaction equation
[C:1]([O:4][CH2:5][C@@H:6]1[C@@H:11]([O:12][C:13](=[O:15])[CH3:14])[C@H:10]([O:16][C:17](=[O:19])[CH3:18])[C@@H:9]([O:20][C:21](=[O:23])[CH3:22])[C@H:8]([N:24]2[C:32]3[C:27](=[C:28]([CH3:33])[CH:29]=[CH:30][CH:31]=3)[C:26]([CH2:34][C:35]3[CH:40]=[CH:39][C:38](Br)=[CH:37][CH:36]=3)=[CH:25]2)[O:7]1)(=[O:3])[CH3:2].[CH2:42]([OH:46])[CH2:43][CH:44]=[CH2:45].C(N(CC)CC)C.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>C(OCC)(=O)C.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(#N)C>[C:1]([O:4][CH2:5][C@@H:6]1[C@@H:11]([O:12][C:13](=[O:15])[CH3:14])[C@H:10]([O:16][C:17](=[O:19])[CH3:18])[C@@H:9]([O:20][C:21](=[O:23])[CH3:22])[C@H:8]([N:24]2[C:32]3[C:27](=[C:28]([CH3:33])[CH:29]=[CH:30][CH:31]=3)[C:26]([CH2:34][C:35]3[CH:40]=[CH:39][C:38](/[CH:45]=[CH:44]/[CH2:43][CH2:42][OH:46])=[CH:37][CH:36]=3)=[CH:25]2)[O:7]1)(=[O:3])[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 4

HCID 8471TriethylamineHCID 693893-Buten-1-olHCID 80271Tri-o-tolylphosphineHCID 671974083-(4-bromophenylmethyl)-4-methyl-1-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)indole

Product 1

HCID 118021778[(2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-[3-[[4-[(E)-4-hydroxybut-1-enyl]phenyl]methyl]-4-methyl-indol-1-yl]tetrahydropyran-2-yl]methyl acetate
Yield 71.9%

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

Combine [(2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-[3-[(4-bromophenyl)methyl]-4-methyl-indol-1-yl]tetrahydropyran-2-yl]methyl acetate (1.67 mmol), 3-buten-1-ol (5 mmol), triethylamine (35.8 mmol), and acetonitrile (10 mL) and purge with nitrogen for 10 minutes. To this mixture add palladium acetate (0.17 mmol) and tri-o-tolylphosphine (0.33 mmol). Heat this mixture at 80° C. for 2 hours, then cool to room temperature. Dilute with ethyl acetate (50 mL) and water (50 mL). Separate and wash the organic phase with brine (50 mL). Dry the organics over sodium sulfate, filter, and concentrate under reduced pressure. Purify by flash chromatography (40 g silica gel cartridge) eluting with 5-80% ethyl acetate in dichloromethane to yield the title compound as a tan foam (0.8 g, 1.2 mmol): MS (m/z): 622.0 (M+H).

Workup

  1. temperaturecool to room temperature
  2. customSeparate
  3. washwash the organic phase with brine (50 mL)
  4. dry with materialDry the organics over sodium sulfate
  5. filtrationfilter
  6. concentrationconcentrate under reduced pressure
  7. customPurify by flash chromatography (40 g silica gel cartridge)
  8. washeluting with 5-80% ethyl acetate in dichloromethane

Sources & evidence

ORD record
ord-984fc17bafb24347a38b71f2a84317a5
Source dataset
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09145435B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes