Triethylamine → tert-butyl [(3S)-1-({[4-(trifluoromethyl)pyridin-2-yl]methoxy}acetyl)pyrrolidin-3-yl]carbamate

HRID 2103408Notes

Reaction equation

HRID 2103408 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]1[CH:8]=[CH:7][N:6]=[C:5]([CH2:9][O:10][CH2:11][C:12]([OH:14])=O)[CH:4]=1.[NH:17]1[CH2:21][CH2:20][C@H:19]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH2:18]1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(CC)CC)C>CN(C=O)C.C(OCC)(=O)C>[F:15][C:2]([F:1])([F:16])[C:3]1[CH:8]=[CH:7][N:6]=[C:5]([CH2:9][O:10][CH2:11][C:12]([N:17]2[CH2:21][CH2:20][C@H:19]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:27])([CH3:26])[CH3:28])[CH2:18]2)=[O:14])[CH:4]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 1514396(3S)-(-)-3-(tert-Butoxycarbonylamino)pyrrolidineHCID 57803266{[4-(Trifluoromethyl)pyridin-2-yl]methoxy}acetic Acid

Product 1

HCID 57803377tert-butyl [(3S)-1-({[4-(trifluoromethyl)pyridin-2-yl]methoxy}acetyl)pyrrolidin-3-yl]carbamateYield 39.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of {[4-(trifluoromethyl)pyridin-2-yl]methoxy}acetic acid (450 mg, 1.9 mmol) and tert-butyl (3S)-pyrrolidin-3-ylcarbamate (360 mg, 1.9 mmol) in DMF (10 mL) was added benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (880 mg, 2.0 mmol) followed by triethylamine (0.80 mL, 5.7 mmol). After being stirred at room temperature overnight, ethyl acetate was added. The solution was washed with 1 N NaOH and water. Purification on silica gel column eluting with EtOAc provided the title compound (300 mg) as a clear oil. MS (M+H) 404.3.

Workup

  1. washThe solution was washed with 1 N NaOH and water
  2. customPurification on silica gel column
  3. washeluting with EtOAc

Sources & evidence

ORD record
ord-af624154e7284e99bb3f9c1b471f81f2
Source dataset
uspto-grants-2009_08
Patent number
US07576089B2

Reaction notes

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