(5S)-3,9,10,11-tetramethoxy-6,7-dihydro-5H-dibenzo[a,c]cyclohepten-5-ylamine → 2-[di(benzyloxy) phosphoryloxy]ethyl N-[(5S)-3,9,10,11-tetramethoxy-6,7-dihydro-5H-dibenzo[a,c]cyclohepten-5-yl]carbamate

HRID 1761239Notes

Reaction equation

HRID 1761239 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:12]3[C:13]([O:21][CH3:22])=[C:14]([O:19][CH3:20])[C:15]([O:17][CH3:18])=[CH:16][C:11]=3[CH2:10][CH2:9][C@H:8]([NH2:23])[C:7]=2[CH:24]=1.[C:25](=O)([O:48]C1C=CC([N+]([O-])=O)=CC=1)[O:26][CH2:27][CH2:28][O:29][P:30]([O:40][CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)([O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:31]>C(#N)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:12]3[C:13]([O:21][CH3:22])=[C:14]([O:19][CH3:20])[C:15]([O:17][CH3:18])=[CH:16][C:11]=3[CH2:10][CH2:9][C@H:8]([NH:23][C:25](=[O:48])[O:26][CH2:27][CH2:28][O:29][P:30]([O:32][CH2:33][C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=3)([O:40][CH2:41][C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)=[O:31])[C:7]=2[CH:24]=1

Participants

4

Reactant 2

HCID 11255953(5S)-3,9,10,11-tetramethoxy-6,7-dihydro-5H-dibenzo[a,c]cyclohepten-5-ylamineHCID 213066252-[Di(benzyloxy)phosphoryloxy]ethyl 4-nitrophenyl carbonate

Product 1

HCID 600781172-[di(benzyloxy) phosphoryloxy]ethyl N-[(5S)-3,9,10,11-tetramethoxy-6,7-dihydro-5H-dibenzo[a,c]cyclohepten-5-yl]carbamateYield 85%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of (5S)-3,9,10,11-tetramethoxy-6,7-dihydro-5H-dibenzo[a,c]cyclohepten-5-ylamine (0.329; 1 mmol) and 2-[di-(benzyloxy)phosphoryloxy]ethyl 4-nitrophenyl carbonate (0.633 g; 1.3 mmol) in acetonitrile (8 ml) was heated at 65° C., under argon atmosphere for 8 hours. After evaporation to dryness, the residue was purified by flash chromatography eluting with a 50-80% gradient of ethyl acetate/petroleum ether to give 2-[di(benzyloxy)phosphoryloxy]ethyl N-[(5S)-3,9,10,11-tetramethoxy-6,7-dihydro-5H-dibenzo[a,c]cyclohepten-5-yl]carbamate.

Workup

  1. customAfter evaporation to dryness
  2. customthe residue was purified by flash chromatography
  3. washeluting with a 50-80% gradient of ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-f20ae2ee32ab403bbf9c34e3972b657a
Source dataset
uspto-grants-2005_01
Patent number
US06846925B2

Reaction notes

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