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Isopropylamine → tert-Butyl ((5S,6R)-6-methyl-2-oxo-5-(2,3,6-trifluorophenyl)piperidin-3-yl)carbamate

HRID 706371
Notes
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Reaction equation

HRID 706371 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:16][CH:17]([C:21]1[C:26]([F:27])=[CH:25][CH:24]=[C:23]([F:28])[C:22]=1[F:29])[C:18](=O)[CH3:19])[C:10](OC(C)C)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].C([NH2:33])(C)C>CS(C)=O>[CH3:19][C@H:18]1[NH:33][C:10](=[O:11])[CH:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH2:16][C@H:17]1[C:21]1[C:26]([F:27])=[CH:25][CH:24]=[C:23]([F:28])[C:22]=1[F:29]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 6363IsopropylamineHCID 89814841Isopropyl 2-(Boc-amino)-5-oxo-4-(2,3,6-trifluorophenyl)hexanoate

Product 1

HCID 89821820tert-Butyl ((5S,6R)-6-methyl-2-oxo-5-(2,3,6-trifluorophenyl)piperidin-3-yl)carbamate

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
55 °C

Procedure

Crude keto ester 19 (23.6 g, 69 wt %, 16.3 g assay, 39 mmol) was dissolved in DMSO (163 mL) and the solution was added to the reactor over 5-10 min. Then the reaction was heated to 55° C. The pH was adjusted to 10.5 according to a handheld pH meter and controlled overnight with an automated pH controller using 8 M aqueous isopropylamine. The reaction was aged for 27.5 hours.

Workup

  1. additionthe solution was added to the reactor over 5-10 min
  2. customwas adjusted to 10.5 according to a handheld pH meter and controlled overnight with an automated pH controller

Sources & evidence

ORD record
ord-6dcc19876acc41bb87f05107a98b0c7b
Source dataset
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09174989B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes