Methanol → HCID 68461426, compound

HRID 501180Notes

Reaction equation

HRID 501180 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[N:7][C:8]([N:11]2[CH2:23][CH2:22][C:21]3[C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[N:14]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C:13]=3[CH2:12]2)=[N:9][CH:10]=1)=O.[H-].C([Al+]CC(C)C)C(C)C.CO.O>C(Cl)Cl>[OH:2][CH2:3][C:5]1[CH:6]=[N:7][C:8]([N:11]2[CH2:23][CH2:22][C:21]3[C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[N:14]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C:13]=3[CH2:12]2)=[N:9][CH:10]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 21225700DiisobutylaluminumhydrideHCID 68461806HCID 68461806, compound

Product 1

HCID 68461426HCID 68461426, compoundYield 75.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of tert-butyl 2-[5-(methoxycarbonyl)pyrimidin-2-yl]-1,2,3,4-tetrahydro-9H-b-carboline-9-carboxylate (3.0 g, 0.0073 moles) in dry DCM (30 mL) was added diisobutyl aluminum hydride (14.7 mL, 0.022 moles, 1.5N in DCM) at −78° C. The temperature was slowly allowed to rise to −25° C. and continued the stirring for further 6.0 hours. After completion of the reaction, MeOH (20 mL) and water (20 mL) was added to the reaction and allowed to come to room temperature. The reaction mixture was then extracted using DCM. The combined organic layer was washed with water (20 mL), brine (20 ml), dried (Na2SO4) and concentrated. The compound was purified by recrystallization using mixture of diethyl ether and hexane to give pure tert-butyl 2-[5-(hydroxymethyl)pyrimidin-2-yl]-1,2,3,4-tetrahydro-9H-b-carboline-9-carboxylate (2.1 g, 75% yield). Rf=0.3. 1H NMR (DMSO-d6, 400 MHz) ppm: 8.38 (s, 2H, 2Ar—H), 8.05 (d, 1H, J=8 Hz, 1—H), 7.49 (d, 1H, J=8 Hz, 1Ar—H), 7.31-7.22 (m, 2H, 2Ar—H), 5.15 (s, 2H, CH2), 5.10 (t, 1H, J=8 Hz, OH), 4.34 (d, 2H, J=8 Hz, CH2), 4.11 (t, 2H, CH2), 2.75 (brs, 2H, CH2), 1.68 (s, 9H, 3CH3). M/e=381 (M+1) (M, 380.440 Calcd. for C21H24N4O3).

Workup

  1. customto rise to −25° C.
  2. customstirring for further 6.0 hours
  3. additionwas added to the reaction
  4. customto come to room temperature
  5. extractionThe reaction mixture was then extracted
  6. washThe combined organic layer was washed with water (20 mL), brine (20 ml)
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated
  9. customThe compound was purified by recrystallization
  10. additionmixture of diethyl ether and hexane

Sources & evidence

ORD record
ord-adb26099d98344c391d7bb14ddc506c9
Source dataset
uspto-grants-2010_08
Patent number
US07772245B2

Reaction notes

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