Tetrabutylammonium Fluoride → 1-Piperidinecarboxylic acid, 2-(2,2-dimethylpropyl)-4-(hydroxymethyl)-, methyl ester

HRID 1963119Notes

Reaction equation

HRID 1963119 reaction equation
[Si]([O:8][CH2:9][CH:10]1[CH2:15][CH2:14][N:13]([C:16]([O:18][CH3:19])=[O:17])[CH:12]([CH2:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH2:11]1)(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>>[OH:8][CH2:9][CH:10]1[CH2:15][CH2:14][N:13]([C:16]([O:18][CH3:19])=[O:17])[CH:12]([CH2:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH2:11]1

Participants

3

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 66731693HCID 66731693, compound

Product 1

HCID 667316611-Piperidinecarboxylic acid, 2-(2,2-dimethylpropyl)-4-(hydroxymethyl)-, methyl ester

Procedure

The compound was prepared as described in Reference Compound 4, Step 4 starting from methyl 4-((tert-butyldimethylsilyloxy)methyl)-2-neopentylpiperidine-1-carboxylate and TBAF (34.2 mL, 34.2 mmol, 1 M in THF). The residue was purified by automated flash column chromatography on a Biotage® KP-SIL 340 g column. A gradient from 30% to 100% EtOAc in heptane was used as eluent, which resulted in the title compound.

Workup

  1. customThe compound was prepared
  2. customThe residue was purified by automated flash column chromatography on a Biotage® KP-SIL 340 g column

Sources & evidence

ORD record
ord-118497b760ee489b8c54f638ec5b1531
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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