Water → 4-Methyl-7-phenoxymethyl-1,2,3,4-tetrahydrocyclopent[b]indole-2-methanol methanesulfonate

HRID 2226936Notes

Reaction equation

HRID 2226936 reaction equation
[C:1]1([CH2:7][O:8][C:9]2[CH:17]=[CH:16][C:15]3N(C)C4CC(CO)CC=4[C:11]=3[CH:10]=2)[CH:6]=CC=[CH:3][CH:2]=1.[CH2:24]([N:26]([CH2:29][CH3:30])[CH2:27][CH3:28])C.[CH3:31][S:32](Cl)(=[O:34])=[O:33].[OH2:36]>ClCCl>[CH3:31][S:32]([O:34][CH2:2][CH:1]1[CH2:7][C:27]2[N:26]([CH3:24])[C:29]3[CH:30]=[CH:6][C:1]([CH2:7][O:8][C:9]4[CH:10]=[CH:11][CH:15]=[CH:16][CH:17]=4)=[CH:2][C:3]=3[C:28]=2[CH2:6]1)(=[O:36])=[O:33]

Participants

6

Reactant 4

HCID 962WaterHCID 8471Triethylamine2×HCID 31297Methanesulfonyl chloride2×HCID 189639931,2,3,4-Tetrahydro-7-phenylmethoxy-4-methycyclopent[b]indole-2-methanol

Product 1

HCID 541962794-Methyl-7-phenoxymethyl-1,2,3,4-tetrahydrocyclopent[b]indole-2-methanol methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a solution of 1,2,3,4-tetrahydro-7-phenylmethoxy-4-methylcyclopent[b]indole-2-methanol (11.2 g, 0.036 mole) and triethylamine (3.39 g, 0.047 mole) and 220 ml of dichloromethane (anhydrous) was added a solution of methanesulfonyl chloride (5.38 g, 0.047 mole) in 27 ml of dichloromethane. After stirring at ambient temperature for 2 hours, additional triethylamine (3.39 g, 0,047 mole) was added, followed by a solution of methanesulfonyl chloride (5.38 g, 3.6 ml, 0,047 mole) in 30 ml of dichloromethane. After stirring for one hour, the mixture was poured into 500 ml of water. The phases were separated and the dichloromethane portion was washed successively with water and saturated sodium chloride solution. The organic phase was dried (anh. MgSO4) and filtered, and the filtrate was concentrated to a dark green oil (15 g). This oil was eluted on silica gel with ethyl acetate/dichloromethane (1:19) via HPLC. The desired fractions were combined and concentrated to give the product as a white solid, 6.27 g, mp. 94°-96° C.

Workup

  1. stirringAfter stirring for one hour
  2. customThe phases were separated
  3. washthe dichloromethane portion was washed successively with water and saturated sodium chloride solution
  4. dry with materialThe organic phase was dried (anh. MgSO4)
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated to a dark green oil (15 g)
  7. washThis oil was eluted on silica gel with ethyl acetate/dichloromethane (1:19) via HPLC
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-070d832f1ace41229217ed0fb4d37872
Source dataset
uspto-grants-1994_09
Patent number
US05350762

Reaction notes

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