Water → HCID 56978727, compound

HRID 2299661Notes

Reaction equation

HRID 2299661 reaction equation
[F:1][CH2:2][O:3][C:4]1[CH:40]=[CH:39][C:7]2[CH2:8][CH2:9][CH2:10][CH:11]([N:13]([CH2:21][C@H:22]([O:31][Si](CC)(CC)CC)[CH2:23][O:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:12][C:6]=2[CH:5]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>O1CCCC1>[F:1][CH2:2][O:3][C:4]1[CH:40]=[CH:39][C:7]2[CH2:8][CH2:9][CH2:10][CH:11]([N:13]([CH2:21][C@H:22]([OH:31])[CH2:23][O:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:14]([O:16][C:17]([CH3:19])([CH3:20])[CH3:18])=[O:15])[CH2:12][C:6]=2[CH:5]=1

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 57079992HCID 57079992, compound

Product 1

HCID 56978727HCID 56978727, compoundYield 94.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under nitrogen, to a solution of N-(3-fluoromethoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)-N-tert-butoxycarbonyl-[(2S)-3-phenoxy-2-(triethylsilyloxy)propyl]-amine (300 mg) in tetrahydrofuran (5 ml) was added tetra-n-butylammonium fluoride (1M in tetrahydrofuran, 0.58 ml) at 5° C., and the mixture was stirred at the same temperature for 15 minutes. The resulting mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and evaporated in vacuo. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=3:1) to give N-(3-fluoromethoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)-N-tert-butoxycarbonyl-[(2S)-2-hydroxy-3-phenoxypropyl]amine (227 mg).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-b942fac21b73416787b213e16b5142a6
Source dataset
uspto-grants-2002_12
Patent number
US06495546B1

Reaction notes

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