2,2,2-Trifluoroethylamine hydrochloride → HCID 131733084, compound

HRID 1518958Notes

Reaction equation

HRID 1518958 reaction equation
N([O-])=O.[Na+].Cl.[F:6][C:7]([F:11])([F:10])[CH2:8]N.[CH2:12]([C@@H:14]1[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][C@H:15]1[OH:27])[CH3:13]>O.C(Cl)Cl.CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O.[Rh+2].[Rh+2]>[C:23]([O:22][C:20]([N:17]1[CH2:18][CH2:19][C@@H:14]([CH2:12][CH3:13])[C@H:15]([O:27][CH2:8][C:7]([F:11])([F:10])[F:6])[CH2:16]1)=[O:21])([CH3:26])([CH3:25])[CH3:24]

Participants

7

Reactant 3

HCID 97722,2,2-Trifluoroethylamine hydrochlorideHCID 23668193Sodium NitriteHCID 58664399HCID 58664399, compound

Product 1

HCID 131733084HCID 131733084, compound

Reagents, catalysts & solvents 3

HCID 152122Dirhodium tetraacetateCatalystHCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Procedure

Add a solution of sodium nitrite (1.8 g, 26.2 mmol in water (7.0 mL) dropwise at ambient temperature to a solution of 2,2,2-trifluoroethylamine hydrochloride (2.9 g, 20.9 mmol) in water (1.7 mL) under nitrogen atmosphere in a 25 mL round bottom flask connected via cannula tube with another round bottom flask containing a solution of trans-tert-butyl 4-ethyl-3-hydroxy-piperidine-1-carboxylate (400 mg, 1.74 mmol), tetrakis(acetato)dirhodium(II) (78 mg, 0.17 mmol) and 500 mg of molecular sieves (3 Å) in DCM (17 mL) under nitrogen atmosphere. Stir the mixture at ambient temperature for 2 hours; filter the mixture; and concentrate the filtrate. Purify the compound by chromatography in a silica gel cartridge eluting with DCM to obtain the title compound as a pale brown waxy solid (140 mg, 75% pure by 1HNMR and can be used without further purification). MS (m/z): 256 (M-tBu+1).

Workup

  1. customconnected via cannula tube with another round bottom flask
  2. filtrationfilter the mixture
  3. concentrationand concentrate the filtrate
  4. customPurify the compound by chromatography in a silica gel cartridge
  5. washeluting with DCM

Sources & evidence

ORD record
ord-b96599acfbad47c582468786b9da429f
Source dataset
uspto-grants-2015_07
Patent number
US09073856B2

Reaction notes

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