Benzyl chloroformate → HCID 131730562, compound

HRID 2090108Notes

Reaction equation

HRID 2090108 reaction equation
[CH:1]1[C:6]2[CH2:7][CH2:8][CH:9]([CH2:12][NH2:13])[CH2:10][CH2:11][C:5]=2[CH:4]=[CH:3][CH:2]=1.[CH:14]1[CH:19]=[CH:18][C:17]([CH2:20][O:21][C:22](Cl)=[O:23])=[CH:16][CH:15]=1.C(N(C(C)C)CC)(C)C>O1CCCC1>[CH2:20]([O:21][C:22](=[O:23])[NH:13][CH2:12][CH:9]1[CH2:8][CH2:7][C:6]2[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=2[CH2:11][CH2:10]1)[C:17]1[CH:18]=[CH:19][CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 81531DiisopropylethylamineHCID 68411636HCID 68411636, compound

Product 1

HCID 131730562HCID 131730562, compoundYield 91.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 1-(6,7,8,9-tetrahydro-5H-benzo[7]annulen-7-yl)methanamine (100 mg, 0.472 mmol) in tetrahydrofuran (5 ml) was added benzyl chloridocarbonate (0.074 ml, 0.520 mmol) and diisopropylethylamine (0.181 ml, 1.039 mmol). The mixture was stirred overnight at 25° C., and then concentrated. The residue was purified by flash chromatography on a Biotage Horizon, 25S column, eluting with 1 column volume of 100% hexanes followed by a gradient of 0 to 100% EtOAc in hexanes over 10 column volumes to provide the title compound (133 mg, 0.430 mmol, 91% yield). Mass spectrum (ESI) 310.1 (M+1).

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by flash chromatography on a Biotage Horizon, 25S column
  3. washeluting with 1 column volume of 100% hexanes

Sources & evidence

ORD record
ord-d61b41b9f7354483b36dccf4ce758d36
Source dataset
uspto-grants-2013_05
Patent number
US08436028B2

Reaction notes

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