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Acetic Acid → (2S)-1-({(1S)-2-[6-(4-Methoxy-phenyl)-2,3-dihydro-indole-1-yl]-1-methyl-ethylamino}-acetyl)-pyrrolidine-2-carbonitrile

HRID 982840
Notes
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Reaction equation

HRID 982840 reaction equation
C(OC(=O)[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)(C)(C)C.C(Cl)Cl.[BH3-][C:33]#[N:34].[Na+].[C:36]([OH:39])(=O)[CH3:37]>C(OCC)(=O)C>[CH3:26][O:25][C:22]1[CH:21]=[CH:20][C:19]([C:16]2[CH:17]=[C:18]3[C:13]([CH2:12][CH2:11][N:10]3[CH2:9][C@@H:8]([NH:7][CH2:37][C:36]([N:10]3[CH2:18][CH2:13][CH2:12][C@H:11]3[C:33]#[N:34])=[O:39])[CH3:27])=[CH:14][CH:15]=2)=[CH:24][CH:23]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6344DichloromethaneHCID 5003444Sodium cyanoborohydrideHCID 67031552(S)-{2-[6-(4-Methoxy-phenyl)-indol-1-yl]-1-methyl-ethyl}-carbamic acid tert-butyl ester

Product 1

HCID 66762315(2S)-1-({(1S)-2-[6-(4-Methoxy-phenyl)-2,3-dihydro-indole-1-yl]-1-methyl-ethylamino}-acetyl)-pyrrolidine-2-carbonitrile

Reagents, catalysts & solvents

1
HCID 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-20e9ccfa55804e2bb98301e40343df5b
Source dataset
uspto-grants-2005_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06861440B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes