Methanol → HCID 15288857, compound

HRID 1613463Notes

Reaction equation

HRID 1613463 reaction equation
[CH3:1][N:2]1[C:10]2[CH:9]=[CH:8][C:7]([OH:11])=[CH:6][C:5]=2[C:4]2[CH2:12][CH2:13][C:14](=[N:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:3]1=2.C(O)(C)C.CO.[BH4-].[Na+]>O>[CH3:1][N:2]1[C:10]2[CH:9]=[CH:8][C:7]([OH:11])=[CH:6][C:5]=2[C:4]2[CH2:12][CH2:13][CH:14]([NH:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:3]1=2

Participants

6

Reactant 4

HCID 887MethanolHCID 3776IsopropanolHCID 4311764Sodium borohydrideHCID 15288858HCID 15288858, compound

Product 1

HCID 15288857HCID 15288857, compoundYield 26.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution prepared from 4-methyl-3-phenylmethylimino-1,2,3,4-tetrahydrocyclopent[b]indol-7-ol (16.0 g), isopropanol (200 ml) and methanol (50 ml) was added sodium borohydride (4.8 g) and the mixture was stirred under nitrogen at ambient temperature for 3 hours. The mixture was cooled to 0° C., water was slowly added and the mixture was stirred 0.5 hour. The mixture was extracted with CH2Cl2 (2×200 ml), and the CH2Cl2 extracts were dried (Na2SO4), concentrated and chromatographed on silica gel eluting with 2:1 hexanes/acetone. The product-containing fractions were combined to give 4.25 grams of 4-methyl-3-(phenylmethylamino)-1,2,3,4-tetrahydrocyclopent[b]indol-7-ol.

Workup

  1. temperatureThe mixture was cooled to 0° C.
  2. stirringthe mixture was stirred 0.5 hour
  3. extractionThe mixture was extracted with CH2Cl2 (2×200 ml)
  4. dry with materialthe CH2Cl2 extracts were dried (Na2SO4)
  5. concentrationconcentrated
  6. customchromatographed on silica gel eluting with 2:1 hexanes/acetone

Sources & evidence

ORD record
ord-581fab5aee114b9183152abb09cb0a67
Source dataset
uspto-grants-1993_03
Patent number
US05192789

Reaction notes

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