Dichloromethane → HCID 19003090, compound

HRID 488096Notes

Reaction equation

HRID 488096 reaction equation
[CH3:1][NH:2][C:3](=[O:22])[O:4][C:5]1[CH:13]=[CH:12][C:11]2[N:10]([CH3:14])[C:9]3[C:15](=[N:18][CH2:19][C:20]#[CH:21])[CH2:16][CH2:17][C:8]=3[C:7]=2[CH:6]=1.C([BH3-])#N.[Na+].C(Cl)[Cl:28]>C(O)(=O)C>[OH2:4].[ClH:28].[CH3:1][NH:2][C:3](=[O:22])[O:4][C:5]1[CH:13]=[CH:12][C:11]2[N:10]([CH3:14])[C:9]3[CH:15]([NH:18][CH2:19][C:20]#[CH:21])[CH2:16][CH2:17][C:8]=3[C:7]=2[CH:6]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 5003444Sodium cyanoborohydrideHCID 19003056HCID 19003056, compound

Product 1

HCID 19003090HCID 19003090, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a stirred solution of 4-methyl-3-(2-propynyl)imino-1,2,3,4-tetrahydrocyclopent[b]indol-7-yl methylcarbamate (1:1 g) in acetic acid (10 ml) was added sodium cyanoborohydride (0.57 g). The reaction was monitored via TLC and after 2 hours, methylene chloride (50 ml) was added and the solution was washed with saturated NaHCO3 until neutral. The methylene chloride layer was dried (Na2SO4), filtered and concentrated. The resulting material was chromatographed on silica gel, eluting with 2:1 hexane/acetone and the pure fractions were collected and concentrated. The resulting solid was dissolved in a minimum amount of EtOAc, diluted with ether and thereafter, ethereal HCl solution was added. The resulting solid was collected via filtration under nitrogen to give 4-methyl-3-(2-propynyl)amino-1,2,3,4,-tetrahydrocyclopent[ b]indol-7-yl methylcarbamate hydrochloride monohydrate (0.4 grams). The reaction was repeated and the products were combined.

Workup

  1. washthe solution was washed with saturated NaHCO3 until neutral
  2. dry with materialThe methylene chloride layer was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe resulting material was chromatographed on silica gel
  6. washeluting with 2:1 hexane/acetone
  7. customthe pure fractions were collected
  8. concentrationconcentrated
  9. dissolutionThe resulting solid was dissolved in a minimum amount of EtOAc
  10. additiondiluted with ether
  11. additionethereal HCl solution was added
  12. filtrationThe resulting solid was collected via filtration under nitrogen

Sources & evidence

ORD record
ord-0e9cb435cae14a4796d664475e8ace03
Source dataset
uspto-grants-1994_03
Patent number
US05298626

Reaction notes

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