Piperidine → Ethyl acetate methanol ammonium hydroxide

HRID 857744Notes

Reaction equation

HRID 857744 reaction equation
ClC1C=CC(N2C=NC=N2)=C(C=1)C[NH:8]C(=O)[C@@H]1CCCN1[C:15]([O:17][CH2:18][CH:19]1C2C=CC=CC=2C2C1=CC=CC=2)=[O:16].N1CCCC[CH2:40]1>CN(C=O)C>[CH3:19][CH2:18][O:17][C:15]([CH3:40])=[O:16].[CH3:15][OH:16].[NH4+:8].[OH-:16]

Participants

4

Reactant 2

HCID 8082PiperidineHCID 69656572N-[5-chloro-2-(1H-1,2,4-triazol-1-yl)benzyl]-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-prolinamide

Product 1

HCID 21901312Ethyl acetate methanol ammonium hydroxide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of N-[5-chloro-2-(1H-1,2,4-triazol-1-yl)benzyl]-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-prolinamide (5.06 g, 9.59 mmol) and piperidine (82 mg, 9.59 mmol, 1 equiv) in DMF (20 mL) was stirred for 3 h at room temperature then concentrated in vacuo. Silica gel chromatography (EtOAc to 8:1:1 EtOAc/MeOH/NH4OH) afforded a sticky, yellow, solid which was dissolved in EtOAc and treated with gaseous HCl for 1 h at 0° C. Solvent was removed in vacuo, and the remaining residue was suspended in ether with vigorous stirring. The resulting precipitate was filtered and washed with ether to afford the title compound as an off-white, hygroscopic powder. 1H NMR (400 MHz, CD3OD): δ 9.79 (s, 1 H), 8.95 (s, 1 H), 7.70 (d, J=1.6 Hz, 1 H), 7.61–7.60 (m, 2 H), 4.44–4.41 (m, 2 H), 4.30 (apparent t, J=7.6 Hz, 1 H), 3.39–3.31 (m, 2 H), 2.46–2.40 (m, 1 H), 2.18–1.92 (m, 3 H). LCMS (M+H): 306.0.

Workup

  1. concentrationthen concentrated in vacuo

Sources & evidence

ORD record
ord-b56af24f843548dea08be79f5288c1e1
Source dataset
uspto-grants-2006_12
Patent number
US07144899B2

Reaction notes

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