1,1,1,3,3,3-Hexafluoro-2-propanol → HCID 70653101, compound

HRID 1467341Notes

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.[F:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1B(O)O.O.[C:26]([OH:30])(=[O:29])[CH:27]=O.C(O)(C(F)(F)F)C(F)(F)F>C(Cl)Cl>[C:10]([O:9][C:8]([NH:7][C@@H:3]1[CH2:4][CH2:5][CH2:6][N:1]([CH:27]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[F:15])[C:26]([OH:30])=[O:29])[CH2:2]1)=[O:14])([CH3:11])([CH3:13])[CH3:12]

Participants

Conditions

Temperature: 120 °C

Procedure

tert-Butyl (3R)-piperidin-3-ylcarbamate (0.1 g, 0.499 mmol), (2-fluorophenyl)boronic acid (0.070 g, 0.499 mmol) and glyoxilic acid monohydrate (0.045 g, 0.499 mmol) were taken up in DCM (2.25 mL)/HFIP (0.25 mL) in a 5 mL microwave vial. The reaction mixture was heated to 120° C. for 15 minutes under microwave irradiation. The solvent was removed in vacuo to give 2-((R)-3-(tert-butoxycarbonylamino)piperidin-1-yl)-2-(2-fluorophenyl)acetic acid as a 1:1 mixture of diastereoisomers.

Workup

customThe solvent was removed in vacuo

Sources & evidence

ORD record: ord-0632563b2a8e47b980db66cfd0fccc35
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08999957B2

Reaction notes

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