Isopropyl chloroformate → propan-2-yl N-(7-cyano-1,2,3,4-tetrahydrocyclopenta[b]indol-2-yl)carbamate

HRID 2427259Notes

Reaction equation

HRID 2427259 reaction equation
[NH2:1][CH:2]1[CH2:15][C:5]2[NH:6][C:7]3[CH:8]=[CH:9][C:10]([C:13]#[N:14])=[CH:11][C:12]=3[C:4]=2[CH2:3]1.C(N(C(C)C)CC)(C)C.Cl[C:26]([O:28][CH:29]([CH3:31])[CH3:30])=[O:27]>C(Cl)Cl.O.C(OCC)C>[CH:29]([O:28][C:26](=[O:27])[NH:1][CH:2]1[CH2:15][C:5]2[NH:6][C:7]3[CH:8]=[CH:9][C:10]([C:13]#[N:14])=[CH:11][C:12]=3[C:4]=2[CH2:3]1)([CH3:31])[CH3:30]

Participants

7

Reactant 3

HCID 7917Isopropyl chloroformateHCID 81531DiisopropylethylamineHCID 468355392-Amino-1,2,3,4-tetrahydrocyclopenta[b]indole-7-carbonitrile

Product 1

HCID 66933210propan-2-yl N-(7-cyano-1,2,3,4-tetrahydrocyclopenta[b]indol-2-yl)carbamateYield 73.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

Under nitrogen, mix (±)-2-amino-1,2,3,4-tetrahydro-cyclopenta[b]indole-7-carbonitrile (7.0 g, 35.5 mmol) with diisopropylethylamine (7.4 mL, 42.6 mmol) in CH2Cl2 (70 mL). Add isopropyl chloroformate (1.0 M in toluene, 42.6 mL, 42.6 mmol) and stir overnight at room temperature. Dilute with water (100 mL) and ethyl ether (50 mL), stir for 10 min and collect the solid. After drying, obtain 7.42 g (61%) of the title compound as a tan solid. MS (m/z): 284 (M+1), 282 (M−1).

Workup

  1. customcollect the solid
  2. customAfter drying

Sources & evidence

ORD record
ord-41c99a38ccb34810b9bae4e998fc9c90
Source dataset
uspto-grants-2011_06
Patent number
US07968587B2

Reaction notes

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