Sodium Hydroxide → HCID 69330119, compound

HRID 2299681Notes

Reaction equation

HRID 2299681 reaction equation
[NH2:1][CH2:2][C@H:3]([OH:12])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[Cl:13][C:14]1[CH:25]=[CH:24][C:17]2[CH2:18][CH2:19][CH2:20][C:21](=O)[CH2:22][C:16]=2[CH:15]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>ClCCCl.C(O)(=O)C>[ClH:13].[Cl:13][C:14]1[CH:25]=[CH:24][C:17]2[CH2:18][CH2:19][CH2:20][CH:21]([NH:1][CH2:2][C@H:3]([OH:12])[CH2:4][O:5][C:6]3[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH2:22][C:16]=2[CH:15]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 1133101(2S)-(-)-1-Amino-3-phenoxy-2-propanolHCID 5049666Sodium triacetoxyborohydrideHCID 21822946HCID 21822946, compound

Product 1

HCID 69330119HCID 69330119, compoundYield 88.3%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 176Acetic AcidSolvent

Procedure

Under nitrogen, to a solution of (2S)-1-amino-3-phenoxy-2-propanol (280 mg) in 1,2-dichloroethane (10 ml) were added 3-chloro-5,7,8,9-tetrahydrobenzocyclohepten-6-one (300 mg), sodium triacetoxyborohydride (820 mg) and acetic acid (0.26 ml) at room temperature, and the mixture was stirred at the same temperature for 6.5 hours. The resulting mixture was poured into aqueous 1N sodium hydroxide 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 (chloroform:methanol=20:1 to 10:1) and followed by treatment with 4N hydrogen chloride in ethyl acetate to give (2S)-1-(3-chloro-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)amino-3-phenoxy-2-propanol hydrochloride (260 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 (chloroform:methanol=20:1 to 10:1)

Sources & evidence

ORD record
ord-0b9e4677378949e1bc08b8fc6408ff18
Source dataset
uspto-grants-2002_12
Patent number
US06495546B1

Reaction notes

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