Dichloromethane → (S)-{2-[6-(4-Methoxy-phenyl)-2,3-dihydro-indol-1-yl]-1-methyl-ethyl}-carbamic-Acid Tert-Butyl Ester

HRID 2249588Notes

Reaction equation

HRID 2249588 reaction equation
[C:1]([O:5][C:6](=[O:28])[NH:7][C@@H:8]([CH3:27])[CH2:9][N:10]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=3)[CH:17]=2)[CH:12]=[CH:11]1)([CH3:4])([CH3:3])[CH3:2].C(Cl)Cl.[BH3-]C#N.[Na+]>C(O)(=O)C.C(OCC)(=O)C>[C:1]([O:5][C:6](=[O:28])[NH:7][C@@H:8]([CH3:27])[CH2:9][N:10]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=3)[CH:17]=2)[CH2:12][CH2:11]1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 5003444Sodium cyanoborohydrideHCID 67031552(S)-{2-[6-(4-Methoxy-phenyl)-indol-1-yl]-1-methyl-ethyl}-carbamic acid tert-butyl ester

Product 1

HCID 20761960(S)-{2-[6-(4-Methoxy-phenyl)-2,3-dihydro-indol-1-yl]-1-methyl-ethyl}-carbamic-Acid Tert-Butyl EsterYield 93.9%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

(S)-{2-[6-(4-Methoxy-phenyl)-indol-1-yl]-1-methyl-ethyl}-carbamic acid tert-butyl ester (1.80 g) was dissolved in acetic acid (25 mL) and CH2Cl2 (10 mL) and cooled to 0° C. NaCNBH3 (1.41 g) was added in portions and the resulting mixture was allowed to stir for 4 hours. The reaction mixture was diluted with ethyl acetate and extracted with concentrated NaOH solution. The organic layer was washed with brine, dried (Na2SO4) and evaporated. The residue was purified by flash chromatography (gradient of ethyl acetate in hexanes) to give the title compound as a brown oil (1.7 g).

Workup

  1. extractionextracted with concentrated NaOH solution
  2. washThe organic layer was washed with brine
  3. dry with materialdried (Na2SO4)
  4. customevaporated
  5. customThe residue was purified by flash chromatography (gradient of ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-6002d3020b384d79a86c7f1f32a6c9cb
Source dataset
uspto-grants-2008_01
Patent number
US07314884B2

Reaction notes

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