Methanol → HCID 59848830, compound

HRID 1096495Notes

Reaction equation

HRID 1096495 reaction equation
[CH3:1][CH:2]1[C:13]2=[C:14]3[C:9](=[CH:10][CH:11]=[C:12]2[OH:15])[NH:8][CH:7]=[C:6]3[CH2:5][CH2:4][NH:3]1.[O:16](C(OC(C)(C)C)=O)[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=O.N1[CH:36]=[CH:35]C=CC=1.C[OH:38]>>[C:35]([O:15][C:12]1[CH:11]=[CH:10][C:9]2[NH:8][CH:7]=[C:6]3[CH2:5][CH2:4][N:3]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:16])[CH:2]([CH3:1])[C:13]=1[C:14]=23)(=[O:38])[CH3:36]

Participants

5

Reactant 4

HCID 887MethanolHCID 1049PyridineHCID 90495Di-tert-butyl dicarbonateHCID 11127338HCID 11127338, compound

Product 1

HCID 59848830HCID 59848830, compound

Procedure

To a solution of 6-methyl-3,4,5,6-tetrahydro-1H-azepino[5,4,3-cd]indol-7-ol, Intermediate 13 (340 mg, 1.7 mmol) in MeOH (10 mL) was added (BOC)2O (513 mg, 2.4 mmol) and the reaction mixture was stirred at room temperature for 30 minutes (95% conversion). Pyridine (0.5 mL) was added and the mixture was left at room temperature over night. The solvent was evaporated at reduced pressure and the resulting residue was dissolved in pyridine (4 mL), cooled on an ice bath, Ac2O (1 mL) was added and the stirred mixture was allowed to slowly reach room temperature over night. The mixture was concentrated under reduced pressure and the residue was co-evaporated twice with toluene. The dark brown oil (0.9 g) was chromatographed on a column of silica, initially with 100% CHCl3 followed by CHCl3/MeOH 99.5/0.5. Evaporation of pure pooled fractions yielded 241 mg of the title compound as a light yellow oil. MS m/z 289 [M+H-isobutene]+.

Workup

  1. waitthe mixture was left at room temperature over night
  2. customThe solvent was evaporated at reduced pressure
  3. dissolutionthe resulting residue was dissolved in pyridine (4 mL)
  4. temperaturecooled on an ice bath
  5. additionAc2O (1 mL) was added
  6. waitthe stirred mixture was allowed to slowly reach room temperature over night
  7. concentrationThe mixture was concentrated under reduced pressure
  8. customThe dark brown oil (0.9 g) was chromatographed on a column of silica, initially with 100% CHCl3
  9. customEvaporation

Sources & evidence

ORD record
ord-5e0362a1b2e64bcb96e5bfbb078fffac
Source dataset
uspto-grants-2012_03
Patent number
US08138333B2

Reaction notes

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