Triethylamine → HCID 19003052, compound

HRID 1613472Notes

Reaction equation

HRID 1613472 reaction equation
[NH2:1][CH:2]1[CH:6]2[N:7]([CH3:15])[C:8]3[CH:9]=[CH:10][C:11]([OH:14])=[CH:12][C:13]=3[CH:5]2[CH2:4][CH2:3]1.C(N(CC)CC)C.Cl[C:24]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:25]>C(Cl)Cl>[CH3:15][N:7]1[C:8]2[CH:9]=[CH:10][C:11]([OH:14])=[CH:12][C:13]=2[CH:5]2[CH2:4][CH2:3][CH:2]([NH:1][C:24]([O:26][CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[O:25])[CH:6]12

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 19003097HCID 19003097, compound

Product 1

HCID 19003052HCID 19003052, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3-amino-1,2,3,3a,4,8b-hexahydro-4-methylcyclopent[b]indol-7-ol (10.7 grams) in methylene chloride (125 ml) was added triethylamine (5.6 grams) followed by the dropwise addition of benzyl chloroformate (10.0 grams) in methylene chloride (25 ml). The mixture was stirred for 2 hours, extracted with water, dried (Na2SO4) and concentrated. The product was purified by chromatography on silica gel, eluting with 2:1 hexane/acetone to provide 1,2,3,3a,4,8b-hexahydro-4-methyl-3-phenylmethoxycarbonylaminocyclopent[b]indol-7-ol.

Workup

  1. extractionextracted with water
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. customThe product was purified by chromatography on silica gel
  5. washeluting with 2:1 hexane/acetone

Sources & evidence

ORD record
ord-b9386d8d88e848f4b8c2f110e70f4d06
Source dataset
uspto-grants-1993_03
Patent number
US05192789

Reaction notes

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