Diisopropylethylamine → Hydrogen Bromide

HRID 1501940Notes

Reaction equation

HRID 1501940 reaction equation
[Br:1]CC(C1C=C2C(=CC=1)C(=O)OCC2)=O.C(N1CCN[C@H](CO)C1)(OC(C)(C)C)=O.[CH:31]([N:34]([CH:37]([CH3:39])[CH3:38])[CH2:35][CH3:36])([CH3:33])[CH3:32]>C1COCC1>[BrH:1].[CH3:36][CH2:35][N:34]([CH:37]([CH3:39])[CH3:38])[CH:31]([CH3:33])[CH3:32]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 24820294tert-butyl (3S)-3-(hydroxymethyl)piperazine-1-carboxylateHCID 86727026HCID 86727026, compound

Product 2

HCID 260Hydrogen BromideHCID 81531Diisopropylethylamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

6-(Bromoacetyl)-3,4-dihydro-1H-isochromen-1-one (˜1.54 g, ˜5.72 mmol, presence of α-chloroketone was noted, ˜10%) and commercially available (S)-4-N—BOC-2-hydroxymethylpiperazine (1.24 g, 5.72 mmol) were added to a round bottom flask and diluted with THF (50 mL). Diisopropylethylamine (1.30 mL, 7.44 mmol) was then introduced and the mixture left stirring for 14 h at RT during which time a considerable amount of solid had formed (presumably HBr salt of DIPEA). The reaction mixture was diluted with EtOAc, then washed with saturated NH4Claq followed by H2O. Both aqueous layers were sequentially back extracted once with another portion of EtOAc, the organics were then combined, dried with MgSO4, filtered, and concentrated in vacuo. The recovered crude product was subjected to purification by flash chromatography (Biotage, 50% EtOAc/Hex) to afford the title compound.

Workup

  1. waitthe mixture left

Sources & evidence

ORD record
ord-77b4f0ce6c0e4a8391a0b795f12cc2ab
Source dataset
uspto-grants-2015_12
Patent number
US09206199B2

Reaction notes

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