Borane;tetrahydrofuran → HCID 11168903, compound

HRID 602766Notes

Reaction equation

HRID 602766 reaction equation
[C:1]1([S:7]([C:10]([CH:26]2[CH2:38][CH2:37][C:36]3[C:35]4[C:30](=[CH:31][CH:32]=[C:33]([Cl:39])[CH:34]=4)[NH:29][C:28]=3[CH2:27]2)([F:25])[C:11]([N:13]([CH2:15][C:16]2[CH:17]=[C:18]([CH:22]=[CH:23][CH:24]=2)[C:19](O)=[O:20])[CH3:14])=[O:12])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.B.C1COCC1>C1COCC1>[C:1]1([S:7]([C:10]([CH:26]2[CH2:38][CH2:37][C:36]3[C:35]4[C:30](=[CH:31][CH:32]=[C:33]([Cl:39])[CH:34]=4)[NH:29][C:28]=3[CH2:27]2)([F:25])[C:11]([N:13]([CH2:15][C:16]2[CH:24]=[CH:23][CH:22]=[C:18]([CH2:19][OH:20])[CH:17]=2)[CH3:14])=[O:12])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 11330553HCID 11330553, compound

Product 1

HCID 11168903HCID 11168903, compoundYield 84.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 61 mg (0.107 mmol) of (RS,SR)-3-({[2-benzenesulfonyl-2-(6-chloro-2,3,4,9-tetrahydro-1H-carbazol-2-yl)-2-fluoro-acetyl]-methyl-amino}-methyl)-benzoic acid (from example 73) in 3 mL of THF at 0° C., 160 μL (0.107 mmol, 1 eq) of BH3.THF (1M in THF) were added, and the reaction mixture stirred for an additional hour, and then partitioned between EtOAc and water. The organic layer was dried over Na2SO4, filtered and evaporated. Column chromatography on silica gel with EtOAc/heptane 2:1 yielded 50 mg (84%) of (RS,SR)-2-benzenesulfonyl-2-(6-chloro-2,3,4,9-tetrahydro-1H-carbazol-2-yl)-2-fluoro-N-(3-hydroxymethyl-benzyl)-N-methyl-acetamide as a white solid, MS: 555 (M).

Workup

  1. custompartitioned between EtOAc and water
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-6470af81657349b581386de38aebb697
Source dataset
uspto-grants-2011_03
Patent number
US07906546B2

Reaction notes

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