Isopropyl chloroformate → HCID 86696478, compound

HRID 870768Notes

Reaction equation

HRID 870768 reaction equation
[C@H:1]12[CH2:7][C@H:4]([NH:5][CH2:6]1)[CH2:3][N:2]2[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9].CCN(C(C)C)C(C)C.Cl[C:25]([O:27][CH:28]([CH3:30])[CH3:29])=[O:26]>C(OCC)(=O)C.C1(C)C=CC=CC=1>[C@H:1]12[CH2:7][C@H:4]([N:5]([C:25]([O:27][CH:28]([CH3:30])[CH3:29])=[O:26])[CH2:6]1)[CH2:3][N:2]2[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9]

Participants

6

Reactant 3

HCID 7917Isopropyl chloroformateHCID 81531DiisopropylethylamineHCID 11521263(1S,4S)-2-Boc-2,5-diazabicyclo[2.2.1]heptane

Product 1

HCID 86696478HCID 86696478, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred, ambient temperature, solution (1S,4S)-tert-butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate [113451-59-5] (1.0 g, 5.0 mmol) and Hunig's base [7087-68-5] (1.4 mL, 8.0 mmol) in ethyl acetate (120 mL) was slowly added a 1.0M solution of isopropyl chloroformate in toluene (5.1 mL) over the course of 10 minutes. The reaction was allowed to stir over night then was washed with brine, dried (MgSO4), and evaporated to obtain 1.3 g of yellow oil. LRMS (ESI) m/z 285.1 [(M+H)]+, calc'd for C14H24N2O4: 284.35.

Workup

  1. washthen was washed with brine
  2. dry with materialdried (MgSO4)
  3. customevaporated

Sources & evidence

ORD record
ord-dad3567e63b8410993ccf4d91381a253
Source dataset
uspto-grants-2015_03
Patent number
US08969565B2

Reaction notes

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