Methyl chloroformate → 3-(Trityl-amino)-piperidine-1-carboxylic acid methyl ester

HRID 2212179Notes

Reaction equation

HRID 2212179 reaction equation
C(N(CC)CC)C.[NH:8]1[CH2:13][CH2:12][CH2:11][CH:10]([NH:14][C:15]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:9]1.Cl[C:35]([O:37][CH3:38])=[O:36]>ClCCl>[CH3:38][O:37][C:35]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([NH:14][C:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:9]1)=[O:36]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 21963705Piperidin-3-yl-trityl-amine

Product 1

HCID 696524093-(Trityl-amino)-piperidine-1-carboxylic acid methyl esterYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add triethylamine (3.73 mL, 26.7 mmol) to a solution of piperidin-3-yl-trityl-amine (7.63 g, 22.3 mmol) in dichloromethane (125 mL), follow by dropwise addition of methyl chloroformate (1.76 mL, 22.7 mmol). Stir the reaction at room temperature under nitrogen overnight. Wash the reaction is wash with saturated aqueous sodium bicarbonate solution, brine, dry over magnesium sulfate and concentrate. Purify by flash chromatography on silica gel (eluting with 0–20% ethyl acetate/hexane) to give 6.51 g of the title compound as a white solid, 73% yield. 1H NMR: consistent with structure.

Workup

  1. customthe reaction at room temperature under nitrogen overnight
  2. washWash the reaction
  3. washis wash with saturated aqueous sodium bicarbonate solution, brine
  4. dry with materialdry over magnesium sulfate
  5. concentrationconcentrate
  6. customPurify by flash chromatography on silica gel (eluting with 0–20% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-30118668cddd478d9d742f3a3cb80f21
Source dataset
uspto-grants-2006_09
Patent number
US07101891B2

Reaction notes

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