Diisopropylethylamine → HCID 59733726, compound

HRID 132108Notes

Reaction equation

HRID 132108 reaction equation
[NH2:1][C:2]1([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([CH3:18])([CH3:17])[CH3:16])[CH:10]=2)[CH2:7][CH2:6][C:5](=[O:8])[CH2:4][CH2:3]1.C(N(C(C)C)CC)(C)C.[C:28](=O)([O:34]C(C)(C)C)[O:29][C:30]([CH3:33])([CH3:32])[CH3:31]>C(Cl)Cl>[C:30]([O:29][C:28](=[O:34])[NH:1][C:2]1([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([CH3:18])([CH3:17])[CH3:16])[CH:10]=2)[CH2:3][CH2:4][C:5](=[O:8])[CH2:6][CH2:7]1)([CH3:33])([CH3:32])[CH3:31]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 10219638Carbonic acid, bis(1,1-dimethylethyl) esterHCID 59733746HCID 59733746, compound

Product 1

HCID 59733726HCID 59733726, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Amino-4-(3-tert-butyl-phenyl)-cyclohexanone (441 mg, 1.8 mmol) was dissolved in dry methylene chloride (10 mL), diisopropylethylamine (0.31 mL, 1.8 mmol) and di-tert-butyl carbonate (400 mg, 1.83 mmol) were added in succession at room temperature. After 19 h, the reaction was concentrated under reduced pressure, and the desired product isolated by chromatography (Rf=0.35 in 20% EtOAc/hexanes). The resulting oil was taken to the next reaction: retention time=2.57 min, method [7]; mass spec (ESI) 369 (24), 368 (100), 272 (42), 211 (24).

Workup

  1. concentrationthe reaction was concentrated under reduced pressure

Sources & evidence

ORD record
ord-46c7de4481ff45ec9384b5493e6ce946
Source dataset
uspto-grants-2008_06
Patent number
US07385085B2

Reaction notes

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