Ammonium Chloride → HCID 86700551, compound

HRID 2203142Notes

Reaction equation

HRID 2203142 reaction equation
[Si:1]([O:18][CH2:19][C@@H:20]1[CH2:25][CH2:24][CH2:23][CH:22](OC)[N:21]1[C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[NH4+]>>[Si:1]([O:18][CH2:19][C@@H:20]1[CH2:25][CH2:24][CH:23]=[CH:22][N:21]1[C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])([C:14]([CH3:16])([CH3:17])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 25517Ammonium ChlorideHCID 86700549HCID 86700549, compound

Product 1

HCID 86700551HCID 86700551, compoundYield 85.7%

Conditions

Temperature
150 °C

Procedure

A mixture of ((2S)-tert-butyl 2-((tert-butyldiphenylsilyloxy)methyl)-6-methoxypiperidine-1-carboxylate (9 g, 18.6 mmol) and ammonium chloride (150 mg, 2.8 mmol) was heated at 150° C. under reduced pressure (50 mbar) for 2 h, cooled to RT, and purified by silica gel chromatography (eluting with 0-10% EtOAc in petroleum ether) to provide the title intermediate (7.2 g).

Workup

  1. temperaturecooled to RT
  2. custompurified by silica gel chromatography (eluting with 0-10% EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-086942e703064dadb647606dbf4dab00
Source dataset
uspto-grants-2016_06
Patent number
US09365549B2

Reaction notes

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