Water → HCID 58658603, compound

HRID 720949Notes

Reaction equation

HRID 720949 reaction equation
[C:1]([NH:4][C@@H:5]1[C:11]2[CH:12]=[C:13]([C:16]([O-])=[O:17])[CH:14]=[CH:15][C:10]=2[C:9]2[C:19]([O:27][CH3:28])=[C:20]([O:25][CH3:26])[C:21]([O:23][CH3:24])=[CH:22][C:8]=2[CH2:7][CH2:6]1)(=[O:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].O>C1COCC1.CCOCC>[OH:17][CH2:16][C:13]1[CH:14]=[CH:15][C:10]2[C:9]3[C:19]([O:27][CH3:28])=[C:20]([O:25][CH3:26])[C:21]([O:23][CH3:24])=[CH:22][C:8]=3[CH2:7][CH2:6][C@H:5]([NH:4][C:1](=[O:3])[CH3:2])[C:11]=2[CH:12]=1.[CH2:1]([NH:4][C@@H:5]1[C:11]2[CH:12]=[C:13]([CH2:16][OH:17])[CH:14]=[CH:15][C:10]=2[C:9]2[C:19]([O:27][CH3:28])=[C:20]([O:25][CH3:26])[C:21]([O:23][CH3:24])=[CH:22][C:8]=2[CH2:7][CH2:6]1)[CH3:2]

Participants

7

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 86605449HCID 86605449, compound

Product 2

HCID 58658570HCID 58658570, compoundYield 33%HCID 58658603HCID 58658603, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of (5S)-5-(acetylamino)-9,10,11-trimethoxy-6,7-dihydro-5H-dibenzo[a,c]cycloheptene-3-carboxylate (2.28 ml; 5.7 mmol) and lithium aluminium hydride (0.216 g; 22.8 mmol) in a mixture of THF (10 ml) and ether (60 ml) was stirred at reflux under argon atmosphere overnight. After addition of water (60 ml), the mixture was stirred for 2 hours. The resulting solid was filtered and the filtrate was evaporated and purified by flash chromatography eluting with a 5–10% gradient of methanol/dichloromethane to give, after evaporation, N-[(5S)-3-hydroxymethyl-9,10,11-trimethoxy-6,7-dihydro-5H-dibenzo[a,c]cyclohepten-5-yl]acetamide (yield: 33%) and [(5S)-5-(ethylamino)-9,10,11-trimethoxy-6,7-dihydro-5H-dibenzo[a,c]cyclohepten-3-yl]methanol (yield: 47%).

Workup

  1. temperatureat reflux under argon atmosphere overnight
  2. stirringthe mixture was stirred for 2 hours
  3. filtrationThe resulting solid was filtered
  4. customthe filtrate was evaporated
  5. custompurified by flash chromatography
  6. washeluting with a 5–10% gradient of methanol/dichloromethane
  7. customto give

Sources & evidence

ORD record
ord-297dbc9125804884b27ae160a5d1faad
Source dataset
uspto-grants-2006_11
Patent number
US07135502B1

Reaction notes

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