Benzyl chloroformate → 1-Benzyl 6-(tert-butyl) 1,6-diazaspiro[3.5]nonane-1,6-dicarboxylate

HRID 525728Notes

Reaction equation

HRID 525728 reaction equation
Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].[C:12]([O:16][C:17]([N:19]1[CH2:27][CH2:26][CH2:25][C:21]2([NH:24][CH2:23][CH2:22]2)[CH2:20]1)=[O:18])([CH3:15])([CH3:14])[CH3:13].CCN(C(C)C)C(C)C>C(Cl)Cl>[N:24]1([C:2]([O:4][CH2:5][C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)=[O:3])[C:21]2([CH2:25][CH2:26][CH2:27][N:19]([C:17]([O:16][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:18])[CH2:20]2)[CH2:22][CH2:23]1

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 81531DiisopropylethylamineHCID 56962132tert-Butyl 1,6-diazaspiro[3.5]nonane-6-carboxylate

Product 1

HCID 582933361-Benzyl 6-(tert-butyl) 1,6-diazaspiro[3.5]nonane-1,6-dicarboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of benzyl chloroformate (0.148 mL, 1.039 mmol) in DCM (1 mL) was added to a mixture of tert-butyl-1,6-diazaspiro[3.5]nonane-6-carboxylate (200 mg, 0.866 mmol) and DIPEA (0.378 mL, 2.165 mmol) in DCM (3 mL) and the mixture was stirred at RT for 16 h. The solvent was evaporated off under reduced pressure and the crude product was purified by flash chromatography (Silica gel column, 4 g, n-hexane/DCM from 20% to 100% DCM) to give the title product as a yellow resin. UPLC-MS (Condition 3) tR=1.21 min, m/z=361.1 [M+H]+.

Workup

  1. customThe solvent was evaporated off under reduced pressure
  2. customthe crude product was purified by flash chromatography (Silica gel column, 4 g, n-hexane/DCM from 20% to 100% DCM)

Sources & evidence

ORD record
ord-03921f909450425895b149a399bb438a
Source dataset
uspto-grants-2016_05
Patent number
US09340537B2

Reaction notes

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