N,N,N',N'-Tetramethylethylenediamine → HCID 86709514, compound

HRID 1848504Notes

Reaction equation

HRID 1848504 reaction equation
[Li+].CC([N-]C(C)C)C.[N:9]1([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:14][CH2:13][CH:12]([C:15]([O:17][CH3:18])=[O:16])[CH2:11][CH2:10]1.CN(CCN(C)C)C.[O:34]=[CH:35][C@@H:36]([NH:38][C:39](=[O:45])[O:40][C:41]([CH3:44])([CH3:43])[CH3:42])[CH3:37]>C1COCC1>[C:41]([O:40][C:39]([NH:38][CH:36]([CH3:37])[CH:35]([C:12]1([C:15]([O:17][CH3:18])=[O:16])[CH2:11][CH2:10][N:9]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:14][CH2:13]1)[OH:34])=[O:45])([CH3:44])([CH3:43])[CH3:42]

Participants

6

Reactant 4

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 3928701-N-Boc-4-Piperidinecarboxylic acid methyl esterHCID 2724682Lithium diisopropylamideHCID 7015728tert-butyl N-((2S)-1-oxopropan-2-yl)carbamate

Product 1

HCID 86709514HCID 86709514, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of LDA (prepared by adding n-BuLi (27.7 mL, 55.5 mmol) to diisopropylamine (8.04 mL, 57.3 mmol) in THF (40 mL) at 0° C., stir for 30 min) was added 1-tert-butyl 4-methyl piperidine-1,4-dicarboxylate (4500 mg, 18.5 mmol) in TMEDA (16.6 mL, 111 mmol) dropwise via syringe pump at −78° C. for 20 min. The mixture was stirred at the same temperature for 30 min, and (S)-tert-butyl (1-oxopropan-2-yl)carbamate (9931 mg, 57.3 mmol) in THF (20 mL) was added slowly by syringe pump for 20 min. The mixture was stirred at −78° C. for 30 min, and quenched with saturated NH4Cl at −78° C., warmed up to rt and diluted with EtOAc (200 mL). The organic layer was separated, and the aqueous layer was extracted with EtOAc (100 mL). The combined organic layers were washed with brine, dried (MgSO4), and concentrated. The residue was purified by column chromatography (MeOH/DCM, gradient 0-10%) to afford the title compound. LC/MS: [(M+1)]+=417

Workup

  1. stirringThe mixture was stirred at −78° C. for 30 min
  2. customquenched with saturated NH4Cl at −78° C.
  3. additiondiluted with EtOAc (200 mL)
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted with EtOAc (100 mL)
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated
  9. customThe residue was purified by column chromatography (MeOH/DCM, gradient 0-10%)

Sources & evidence

ORD record
ord-c8f8145cedd848c980796b0485618e13
Source dataset
uspto-grants-2015_02
Patent number
US08952166B2

Reaction notes

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