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

Ethyl trifluoroacetate → (1R,3S,4S)-3-[(2,2,2-Trifluoro-acetylamino)-methyl]-2-aza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester

HRID 882796
Notes
Print preview

Reaction equation

HRID 882796 reaction equation
[F:1][C:2]([F:9])([F:8])[C:3]([O:5]CC)=O.[C:10]([O:14][C:15]([N:17]1[C@H:22]([CH2:23][NH2:24])[C@@H:21]2[CH2:25][C@H:18]1[CH2:19][CH2:20]2)=[O:16])([CH3:13])([CH3:12])[CH3:11].CCN(C(C)C)C(C)C>C1COCC1>[C:10]([O:14][C:15]([N:17]1[C@H:22]([CH2:23][NH:24][C:3](=[O:5])[C:2]([F:1])([F:8])[F:9])[C@@H:21]2[CH2:25][C@H:18]1[CH2:19][CH2:20]2)=[O:16])([CH3:13])([CH3:11])[CH3:12]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 9794Ethyl trifluoroacetateHCID 81531DiisopropylethylamineHCID 66866957tert-butyl (1R,3S,4S)-3-(aminomethyl)-2-azabicyclo[2.2.1]heptane-2-carboxylate

Product 1

HCID 86649700(1R,3S,4S)-3-[(2,2,2-Trifluoro-acetylamino)-methyl]-2-aza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Procedure

Ethyl trifluoroacetate (12.2 mmol, 1.30 eq) is added to a solution of (1R,3S,4S)-3-aminomethyl-2-aza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester (9.42 mmol, 1.00 eq) and DIPEA (14.1 mmol, 1.50 eq) in THF (25 mL). After 50 min the mixture is concentrated in vacuo, diluted with TBME (100 mL) and washed twice with aq. citric acid (5%) and water respectively. The organic layer is dried over MgSO4 and concentrated in vacuo to give a crude product which is used without further purification. LC-MS (basic): tR=0.95 min; [M+H]+=323.2.

Workup

  1. concentrationAfter 50 min the mixture is concentrated in vacuo
  2. additiondiluted with TBME (100 mL)
  3. washwashed twice with aq. citric acid (5%) and water respectively
  4. dry with materialThe organic layer is dried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f3b1a520da93430fac43de711a19aa10
Source dataset
uspto-grants-2012_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08236801B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes