9-Fluorenylmethyl chloroformate → HCID 68686362, compound

HRID 2244269Notes

Reaction equation

HRID 2244269 reaction equation
[CH:1]1[CH:2]=[CH:3][N:4]2[CH2:10][C:9]3[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=3[NH:7][CH2:6][C:5]=12.C(N(CC)C(C)C)(C)C.Cl[C:25]([O:27][CH2:28][CH:29]1[C:41]2[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=2[C:35]2[C:30]1=[CH:31][CH:32]=[CH:33][CH:34]=2)=[O:26]>ClCCl.C(OCC)C>[CH:40]1[C:41]2[CH:29]([CH2:28][O:27][C:25]([N:7]3[C:8]4[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=4[CH2:10][N:4]4[CH:3]=[CH:2][CH:1]=[C:5]4[CH2:6]3)=[O:26])[C:30]3[C:35](=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:36]=2[CH:37]=[CH:38][CH:39]=1

Participants

6

Reactant 3

HCID 343679-Fluorenylmethyl chloroformateHCID 81531DiisopropylethylamineHCID 1554704810,11-Dihydro-5H-benzo[e]pyrrolo[1,2-a][1,4]diazepine

Product 1

HCID 68686362HCID 68686362, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine (19.23 g, 0.104 mol) and N,N-diisopropylethylamine (27.3 mL, 0.157 mol) in dichloromethane (500 mL) was added 9-fluorenylmethyl chloroformate (27 g, 0.104 mol). The reaction mixture was stirred at room temperature under nitrogen for 4 hours, and then washed with 1 M hydrochloric acid (3×300 mL), water (300 mL) and brine (300 mL), dried over anhydrous magnesium sulfate, and concentrated in vacuo to give a pale yellow solid. The solid was slurried in dichloromethane (75 mL), the slurry was diluted with diethyl ether (300 mL) and the resulting white suspension stirred overnight. Filtration afforded the title compound (34.64 g, 82%) as a white solid, m.p. 141-142° C.

Workup

  1. washwashed with 1 M hydrochloric acid (3×300 mL), water (300 mL) and brine (300 mL)
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customto give a pale yellow solid
  5. stirringthe resulting white suspension stirred overnight
  6. filtrationFiltration

Sources & evidence

ORD record
ord-e03f10032da046cf84b1fbb2064f426b
Source dataset
uspto-grants-2010_03
Patent number
US07678787B2

Reaction notes

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