HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Triethylamine → HCID 86602058, compound

HRID 1295373
Notes
Print preview

Reaction equation

HRID 1295373 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11608744(S)-N-Methyl-1-[3,5-bis(trifluoromethyl)phenyl]ethylamineHCID 86602055HCID 86602055, compound

Product 1

HCID 86602058HCID 86602058, compoundYield 19.6%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

To racemic Intermediate 40, one enantiomer being (1S,2S)-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 (0.24 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 stirred 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 (0.06 g, 19% 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-3e924b622c9e4462b866a967d1aecfb1
Source dataset
uspto-grants-2007_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07241798B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes