Methyl iodide → (RS,SR)-2-(1-benzenesulfonyl-2-methoxy-1-methyl-ethyl)-6-chloro-9-methoxymethyl-2,3,4,9-tetrahydro-1H-carbazole

HRID 602757Notes

Reaction equation

HRID 602757 reaction equation
[C:1]1([S:7]([C:10]([CH:14]2[CH2:26][CH2:25][C:24]3[C:23]4[C:18](=[CH:19][CH:20]=[C:21]([Cl:27])[CH:22]=4)[N:17]([CH2:28][O:29][CH3:30])[C:16]=3[CH2:15]2)([CH3:13])[CH2:11][OH:12])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[CH3:33]I>C1COCC1>[C:1]1([S:7]([C:10]([CH:14]2[CH2:26][CH2:25][C:24]3[C:23]4[C:18](=[CH:19][CH:20]=[C:21]([Cl:27])[CH:22]=4)[N:17]([CH2:28][O:29][CH3:30])[C:16]=3[CH2:15]2)([CH3:13])[CH2:11][O:12][CH3:33])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 67266793(RS,SR)-2-benzenesulfonyl-2-(6-chloro-9-methoxymethyl-2,3,4,9-tetrahydro-1H-carbazol-2-yl)-propan-1-ol

Product 1

HCID 67266821(RS,SR)-2-(1-benzenesulfonyl-2-methoxy-1-methyl-ethyl)-6-chloro-9-methoxymethyl-2,3,4,9-tetrahydro-1H-carbazoleYield 72%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

130 mg (0.29 mmol) of (RS,SR)-2-benzenesulfonyl-2-(6-chloro-9-methoxymethyl-2,3,4,9-tetrahydro-1H-carbazol-2-yl)-propan-1-ol in 5 mL of THF at 0° C. were treated with 14 mg (0.32 mmol, 1.1 eq) of NaH (55% in oil) portionwise within 30 min. 30 min. 30 μL (0.43 mmol, 1.5 eq) of MeI were added and the reaction mixture was stirred an additional 2 hours, partitioned between EtOAc and a saturated aqueous solution of NH4Cl. The organic phase was washed with brine, dried over Na2SO4, and evaporated. Column chromatography with heptane/EtOAc 1:2 gave 96 mg (72%) of (RS,SR)-2-(1-benzenesulfonyl-2-methoxy-1-methyl-ethyl)-6-chloro-9-methoxymethyl-2,3,4,9-tetrahydro-1H-carbazole as a white solid, MS: 479 (MNH4+).

Workup

  1. custom30 min
  2. custompartitioned between EtOAc
  3. washThe organic phase was washed with brine
  4. dry with materialdried over Na2SO4
  5. customevaporated

Sources & evidence

ORD record
ord-23fc9b7f5f564458921e02e567c09c7a
Source dataset
uspto-grants-2011_03
Patent number
US07906546B2

Reaction notes

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