Isopropyl chloroformate → HCID 118037470, compound

HRID 715588Notes

Reaction equation

HRID 715588 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:4][CH2:3]1.C(N(CC)CC)C.Cl[C:26]([O:28][CH:29]([CH3:31])[CH3:30])=[O:27]>ClCCl>[CH:29]([O:28][C:26]([NH:1][CH:2]1[CH2:3][CH2:4][N:5]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:6][CH2:7]1)=[O:27])([CH3:31])[CH3:30]

Participants

5

Reactant 3

HCID 7917Isopropyl chloroformateHCID 8471TriethylamineHCID 178466404-Amino-1-N-Cbz-piperidine

Product 1

HCID 118037470HCID 118037470, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Benzyl 4-aminopiperidine-1-carboxylate (100 mg) and triethylamine (190 μL) are dissolved in dichloromethane (2 mL), treated with isopropyl chloroformate (920 μL, 1 M solution in toluene) and stirred for 2 hours at room temperature. The mixture is partitioned between dichloromethane and saturated aqueous NH4Cl solution. The organic phase is dried (MgSO4) and concentrated. The residue is purified by HPLC on reversed phase to give the title compound. LC (method 1): tR=1.02 min; Mass spectrum (ESI+): m/z=321 [M+H]+.

Workup

  1. customThe mixture is partitioned between dichloromethane and saturated aqueous NH4Cl solution
  2. dry with materialThe organic phase is dried (MgSO4)
  3. concentrationconcentrated
  4. customThe residue is purified by HPLC on reversed phase

Sources & evidence

ORD record
ord-77c5ddb7aeae489fa008281b4e8b9953
Source dataset
uspto-grants-2015_11
Patent number
US09187477B2

Reaction notes

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