Triisopropyl borate → tert-butyl 4-(1H-indol-5-ylamino)piperidine-1-carboxylate

HRID 20983Notes

Reaction equation

HRID 20983 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]([C:22]2[CH:23]=[C:24]3[C:28](=[CH:29][CH:30]=2)[N:27](C(OC(C)(C)C)=O)[CH:26]=[CH:25]3)C(OC(C)(C)C)=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].B(OC(C)C)(OC(C)C)OC(C)C.[Li+].CC([N-]C(C)C)C.CCCCCCC.C1COCC1.C(C1C=CC=CC=1)C>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:22]2[CH:23]=[C:24]3[C:28](=[CH:29][CH:30]=2)[NH:27][CH:26]=[CH:25]3)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 21531Triisopropyl borateHCID 684933161h-Indole-1-carboxylic acid,5-[[(1,1-dimethylethoxy)carbonyl][1-[(1,1-dimethylethoxy)carbonyl]-4-piperidinyl]amino]-,1,1-dimethylethyl esterHCID 86590273LDA THF ethylbenzene heptane

Product 1

HCID 66650318tert-butyl 4-(1H-indol-5-ylamino)piperidine-1-carboxylateYield 62%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a similar manner to Step 2 of Reference Example 1, 5-[1-(tert-butoxycarbonyl)-4-piperidyl-N-(tert-butoxycarbonyl)amino]-1-(tert-butoxycarbonyl)indole (320 mg, 0.621 mmol) was dissolved in THF (5 mL), and the solution was treated with triisopropyl borate (0.215 mL, 0.932 mmol) and LDA-heptane/THF/ethylbenzene solution (2.0 mol/L, 0.776 mL, 1.55 mmol), followed by purification by slurry using hexane to obtain Compound BQ (177 mg, yield 62%).

Workup

  1. customfollowed by purification by slurry
  2. customto obtain Compound BQ (177 mg, yield 62%)

Sources & evidence

ORD record
ord-7d2b35a6fcc24718a1fedb310af22cd2
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Reaction notes

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