Sodium cyanoborohydride → tert-butyl 4-(2,3-dihydro-1H-indol-7-yl)piperazine-1-carboxylate

HRID 1371518Notes

Reaction equation

HRID 1371518 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:15]=[CH:16][CH:17]=[C:18]3[C:22]=2[NH:21][CH:20]=[CH:19]3)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([BH3-])#N.[Na+]>C(O)(=O)C.C(Cl)Cl.[OH-].[Na+]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:15]=[CH:16][CH:17]=[C:18]3[C:22]=2[NH:21][CH2:20][CH2:19]3)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 2

HCID 5003444Sodium cyanoborohydrideHCID 21070951tert-butyl 4-(1H-indol-7-yl)piperazine-1-carboxylate

Product 1

HCID 21070950tert-butyl 4-(2,3-dihydro-1H-indol-7-yl)piperazine-1-carboxylateYield 46%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolvent

Procedure

7-(4-t-Butyloxycarbonylpiperazin-1-yl)indole (200 mg, 0.67 mmol) is dissolved in acetic acid (4 mL). To the solution, sodium cyanoborohydride (84 mg, 1.33 mmol) is added. The reaction mixture is stirred for about 2 hours at r.t. The mixture is then diluted with DCM and NaOH (1M) is added. The organic layer is separated, dried and concentrated. The residue is chromatographed on the silica gel and the product containing fractions are combined to give about 93 mg of the 7-(4-t-butyloxycarbonylpiperazin-1-yl)-2,3-dihydroindole (46%).

Workup

  1. additionis added
  2. customThe organic layer is separated
  3. customdried
  4. concentrationconcentrated
  5. customThe residue is chromatographed on the silica gel
  6. additionthe product containing fractions

Sources & evidence

ORD record
ord-d0406b2b6c834bf7a4c9eaf99970312d
Source dataset
uspto-grants-2007_01
Patent number
US07157463B2

Reaction notes

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