Diisopropylethylamine → HCID 70652638, compound

HRID 1467349Notes

Reaction equation

HRID 1467349 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][C@@H:3]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH2:2]1.Br[CH:16]([C:21]1[C:26]([F:27])=[CH:25][CH:24]=[CH:23][C:22]=1[F:28])[C:17]([O:19][CH3:20])=[O:18].CCN(C(C)C)C(C)C>CC#N>[C:10]([O:9][C:8]([NH:7][C@@H:3]1[CH2:4][CH2:5][CH2:6][N:1]([C@@H:16]([C:21]2[C:22]([F:28])=[CH:23][CH:24]=[CH:25][C:26]=2[F:27])[C:17]([O:19][CH3:20])=[O:18])[CH2:2]1)=[O:14])([CH3:11])([CH3:13])[CH3:12].[C:10]([O:9][C:8]([NH:7][C@@H:3]1[CH2:4][CH2:5][CH2:6][N:1]([C@H:16]([C:21]2[C:22]([F:28])=[CH:23][CH:24]=[CH:25][C:26]=2[F:27])[C:17]([O:19][CH3:20])=[O:18])[CH2:2]1)=[O:14])([CH3:11])([CH3:13])[CH3:12]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 1514172(3R)-3-Aminopiperidine, 3-BOC protectedHCID 86681288HCID 86681288, compound

Product 2

HCID 70652638HCID 70652638, compoundHCID 86681289HCID 86681289, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
90 °C

Procedure

tert-Butyl (3R)-piperidin-3-ylcarbamate (0.234 g, 1.168 mmol), methyl bromo(2,6-difluorophenyl)acetate (0.434 g, 1.636 mmol) and DIPEA (0.612 mL, 3.51 mmol) were taken up in MeCN (11 mL) in a 20 mL microwave vial. The reaction was stirred at 90° C. for 18 hours. Room temperature was attained, and the solvent removed in vacuo. Purification of the residue by MPLC (6-50% EtOAc-hexanes) gave (S)-methyl 2-((R)-3-(tert-butoxycarbonylamino)piperidin-1-yl)-2-(2,6-difluorophenyl)-acetate as a yellow gum and (R)-methyl 2-((R)-3-(tert-butoxycarbonylamino)piperidin-1-yl)-2-(2,6-difluorophenyl)acetate as a yellow gum (R,R).

Workup

  1. customRoom temperature
  2. customthe solvent removed in vacuo
  3. customPurification of the residue by MPLC (6-50% EtOAc-hexanes)

Sources & evidence

ORD record
ord-35184d8caff04238b7577466b440eb6f
Source dataset
uspto-grants-2015_04
Patent number
US08999957B2

Reaction notes

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