Benzyl chloroformate → HCID 89665651, compound

HRID 2174675Notes

Reaction equation

HRID 2174675 reaction equation
[NH2:1][CH2:2][C@@H:3]1[CH2:9][C:6]2([CH2:8][CH2:7]2)[CH2:5][N:4]1[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11].CCN(C(C)C)C(C)C.[CH2:26]([O:33][C:34](Cl)=[O:35])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C(#N)C.C(Cl)Cl>[CH2:26]([O:33][C:34]([NH:1][CH2:2][C@@H:3]1[CH2:9][C:6]2([CH2:7][CH2:8]2)[CH2:5][N:4]1[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[O:35])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

6

Reactant 3

HCID 10387Benzyl chloroformateHCID 81531DiisopropylethylamineHCID 66847925(S)-tert-butyl 6-(aminomethyl)-5-azaspiro[2.4]heptane-5-carboxylate

Product 1

HCID 89665651HCID 89665651, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-tert-butyl 6-(aminomethyl)-5-azaspiro[2.4]heptane-5-carboxylate (prepared according to WO2011006960; 136 mg, 0.6 mmol) in acetonitrile (1.5 ml), DIPEA (156 μl, 0.9 mmol) and benzylchloroformate (100 μl, 0.7 mmol) were added. After 1 h at RT the reaction was diluted with DCM (20 ml) and washed with an aqueous satd. solution of NH4Cl; organics were evaporated to obtain an oil, which was purified on silica gel column (Cyclohexane/AcOEt from 9/1 to 7/3). Yield 168 mg, transparent oil.

Workup

  1. washwashed with an aqueous satd
  2. customorganics were evaporated
  3. customto obtain an oil, which
  4. customwas purified on silica gel column (Cyclohexane/AcOEt from 9/1 to 7/3)

Sources & evidence

ORD record
ord-c5e352f2b8294581bfe1c324702fa136
Source dataset
uspto-grants-2015_06
Patent number
US09062033B2

Reaction notes

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