Triethylamine → HCID 86602056, compound

HRID 1295372Notes

Reaction equation

HRID 1295372 reaction equation
[CH2:1]([N:8]1[CH2:13][CH:12]2[C@:10]([C:14](Cl)=[O:15])([CH2:11]2)[C@H:9]1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[F:30][C:31]([F:47])([F:46])[C:32]1[CH:33]=[C:34]([C@@H:42]([NH:44][CH3:45])[CH3:43])[CH:35]=[C:36]([C:38]([F:41])([F:40])[F:39])[CH:37]=1>C(=O)(O)[O-].[Na+]>[F:30][C:31]([F:46])([F:47])[C:32]1[CH:33]=[C:34]([C@@H:42]([N:44]([CH3:45])[C:14]([C@:10]23[CH2:11][CH:12]2[CH2:13][N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C@@H:9]3[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:15])[CH3:43])[CH:35]=[C:36]([C:38]([F:39])([F:40])[F:41])[CH:37]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11608744(S)-N-Methyl-1-[3,5-bis(trifluoromethyl)phenyl]ethylamineHCID 86602057HCID 86602057, compound

Product 1

HCID 86602056HCID 86602056, compoundYield 18.3%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

To racemic Intermediate 40, one enantiomer being (1R,2R)-3-benzyl-2-phenyl-3-aza-bicyclo[3.1.0]hexane-1-carbonyl chloride (0.17 g, 0.56 mmol) in MC (5 mL) was added triethylamine (0.23 mL, 1.7 mmol) and (S)-1-(3,5-bis(trifluoromethyl)phenyl)-N-methylethanamine 0.15 g, 0.56 mmol) in MC (1 mL). The reaction was allowed to stir at room temperature overnight. The reaction was diluted with saturated sodium bicarbonate solution and the phases separated. The organics were washed with brine, dried over sodium sulfate, filtered, and concentrated to an oil. This material was flash chromatographed on silica using a gradient of 5 to 10% EtOAc/Hexanes to afford the title compound (0.056 g, 18% yield).

Workup

  1. customthe phases separated
  2. washThe organics were washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to an oil
  6. customchromatographed on silica using a gradient of 5 to 10% EtOAc/Hexanes

Sources & evidence

ORD record
ord-fd9b95d4cb33476c8812779061c2a6c5
Source dataset
uspto-grants-2007_07
Patent number
US07241798B2

Reaction notes

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