Diisopropylethylamine → N-[2-benzyloxy-5-[(1R)-1-hydroxy-2-(3-methoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-ylamino)ethyl]phenyl]methanesulfonamide

HRID 1351906Notes

Reaction equation

HRID 1351906 reaction equation
[CH3:1][O:2][C:3]1[CH:14]=[CH:13][C:6]2[CH2:7][CH2:8][CH2:9][CH:10]([NH2:12])[CH2:11][C:5]=2[CH:4]=1.[CH2:15]([O:22][C:23]1[CH:28]=[CH:27][C:26]([C@@H:29]([O:32][Si](CC)(CC)CC)[CH2:30]I)=[CH:25][C:24]=1[NH:40][S:41]([CH3:44])(=[O:43])=[O:42])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(N(CC)C(C)C)(C)C.S([O-])(O)=O.[Na+]>CN(C)C(=O)C>[CH2:15]([O:22][C:23]1[CH:28]=[CH:27][C:26]([C@@H:29]([OH:32])[CH2:30][NH:12][CH:10]2[CH2:9][CH2:8][CH2:7][C:6]3[CH:13]=[CH:14][C:3]([O:2][CH3:1])=[CH:4][C:5]=3[CH2:11]2)=[CH:25][C:24]=1[NH:40][S:41]([CH3:44])(=[O:42])=[O:43])[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 180073203-methoxy-6,7,8,9-tetrahydro-5H-benzo[7]annulen-6-amineHCID 23665763Sodium BisulfiteHCID 54211801(R)-N-[2-benzyloxy-5-(2-iodo-1-triethylsilyloxyethyl)phenyl]methanesulfonamide

Product 1

HCID 18340078N-[2-benzyloxy-5-[(1R)-1-hydroxy-2-(3-methoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-ylamino)ethyl]phenyl]methanesulfonamideYield 20%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

Under nitrogen, a solution of 3-methoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-ylamine (720 mg), N-[2-benzyloxy-5-[(1R)-2-iodo-1-(triethylsilyloxy)ethyl]phenyl]-methanesulfonamide (2.1 g) and N,N-diisopropylethylamine (2.6 ml) in N,N-dimethylacetamide (10 ml) was stirred at 110° C. for 96 hours. The resulting mixture was poured into aqueous 10% sodium hydrogensulfite and extracted with ethyl acetate. The organic layer was successively washed with saturated aqueous sodium hydrogencarbonate and brine, dried over anhydrous sodium sulfate and evaporated in vacuo. The residue was purified by column chromatography on silica gel (chloroform:methanol=40:1 to 20:1) to give N-[2-benzyloxy-5-[(1R)-1-hydroxy-2-(3-methoxy-6,7,8,9-tetrahydro-5H-benzo-cyclohepten-6-ylamino)ethyl]phenyl]methanesulfonamide (381 mg).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was successively washed with saturated aqueous sodium hydrogencarbonate and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customevaporated in vacuo
  5. customThe residue was purified by column chromatography on silica gel (chloroform:methanol=40:1 to 20:1)

Sources & evidence

ORD record
ord-e9f6eddc4abf4dff933ded879c523324
Source dataset
uspto-grants-2007_05
Patent number
US07217706B2

Reaction notes

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