Water → HCID 58017420, compound

HRID 451988Notes

Reaction equation

HRID 451988 reaction equation
[NH2:1][CH2:2][CH2:3][O:4][C@@H:5]([C:19]1[CH:20]=[C:21]([CH3:25])[CH:22]=[CH:23][CH:24]=1)[C@@H:6]1[CH2:11][CH2:10][CH2:9][N:8]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:7]1.Cl[C:27]([O:29][CH3:30])=[O:28].O>CN(C1C=CN=CC=1)C.C(Cl)Cl.CCN(CC)CC>[CH3:30][O:29][C:27]([NH:1][CH2:2][CH2:3][O:4][C@@H:5]([C:19]1[CH:20]=[C:21]([CH3:25])[CH:22]=[CH:23][CH:24]=1)[C@@H:6]1[CH2:11][CH2:10][CH2:9][N:8]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:7]1)=[O:28]

Participants

7

Reactant 3

HCID 962WaterHCID 6586Methyl chloroformateHCID 58017425HCID 58017425, compound

Product 1

HCID 58017420HCID 58017420, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Conditions

Temperature
2.5 °C

Procedure

To a solution of (R)-tert-butyl 3-((R)-(2-aminoethoxy)(m-tolyl)methyl)piperidine-1-carboxylate and DMAP in anhydrous CH2Cl2, Et3N was added. The resulting mixture was cooled to 0-5° C. under ice-water bath, a solution of methyl chloroformate in anhydrous CH2Cl2 was added dropwise. After addition, the reaction mixture was stirred for 1-2 hr at 0-5° C. Water was added to quench the reaction. The aqueous layer was extracted with CH2Cl2, the combined organic layers were washed with 10% citric acid and brine, then dried over Na2SO4, filtered and concentrated to the crude product, which was purified by preparative TLC to afford (R)-tert-butyl 3-((R)-(2-(methoxycarbonylamino)ethoxy)(m-tolyl)methyl)piperidine-1-carboxylate.

Workup

  1. additionAfter addition
  2. customto quench
  3. customthe reaction
  4. extractionThe aqueous layer was extracted with CH2Cl2
  5. washthe combined organic layers were washed with 10% citric acid and brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated to the crude product, which
  9. customwas purified by preparative TLC

Sources & evidence

ORD record
ord-6217bef6e5ee4718b57a95acb032ee26
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Reaction notes

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