Potassium Carbonate → 1,2,3,4-Tetrahydro-2-hydroxymethyl-4-methylcyclopent[b]indol-7-yl methylcarbamate

HRID 2226935Notes

Reaction equation

HRID 2226935 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:16][C:6]2[N:7]([CH3:15])[C:8]3[CH:9]=[CH:10][C:11]([OH:14])=[CH:12][C:13]=3[C:5]=2[CH2:4]1.C([O-])([O-])=O.[K+].[K+].[CH3:23][N:24]=[C:25]=[O:26]>O1CCCC1>[CH3:23][NH:24][C:25](=[O:26])[O:14][C:11]1[CH:10]=[CH:9][C:8]2[N:7]([CH3:15])[C:6]3[CH2:16][CH:3]([CH2:2][OH:1])[CH2:4][C:5]=3[C:13]=2[CH:12]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 12228Methyl IsocyanateHCID 189639901,2,3,4-Tetrahydro-2-hydroxymethyl-4-methylcyclopent[b]indol-7-ol

Product 1

HCID 189640201,2,3,4-Tetrahydro-2-hydroxymethyl-4-methylcyclopent[b]indol-7-yl methylcarbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 1,2,3,4-tetrahydro-2-hydroxymethyl-4-methylcyclopent[b]indol-7-ol (1.7 g, 0.008 mole) in 50 ml of tetrahydrofuran was added milled K2CO3 (2.0 g, 0.015 mole), followed by a solution of methylisocyanate (0.5 ml, 0.008 mole) in 5 ml of tetrahydrofuran. After stirring at ambient temperature for two hours, the mixture was filtered and the filtrate concentrated to a yellow solid. This material was eluted on a silica gel column with ethyl acetate/dichloromethane (1:2) via HPLC. The desired fractions were combined and concentrated to a white solid, 2.1 g, m.p. 134°-8° C. This material was recrystallized from methanol/ether (1:10) to give the product as a white solid, 1.5 g, m.p. 137°-8° C.

Workup

  1. filtrationthe mixture was filtered
  2. concentrationthe filtrate concentrated to a yellow solid
  3. washThis material was eluted on a silica gel column with ethyl acetate/dichloromethane (1:2) via HPLC
  4. concentrationconcentrated to a white solid, 2.1 g, m.p. 134°-8° C
  5. customThis material was recrystallized from methanol/ether (1:10)

Sources & evidence

ORD record
ord-e06d34adab934b968f69c3944ff4f3c3
Source dataset
uspto-grants-1994_09
Patent number
US05350762

Reaction notes

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