2,2,2-Trifluoroethanol → HCID 86710530, compound

HRID 341556Notes

Reaction equation

HRID 341556 reaction equation
N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O.[OH:17][C@H:18]1[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19]1.[F:30][C:31]([F:35])([F:34])[CH2:32]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[F:30][C:31]([F:35])([F:34])[CH2:32][O:17][C@@H:18]1[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19]1

Participants

6

Reactant 4

HCID 64092,2,2-TrifluoroethanolHCID 11776TriphenylphosphineHCID 97268Di-tert-butyl azodicarboxylateHCID 854055tert-Butyl (3S)-3-hydroxypyrrolidine-1-carboxylate

Product 1

HCID 86710530HCID 86710530, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Di-tert-butyl azodicarboxylate (2.96 g, 12.83 mmol) was added to an ice cooled mixture of tert-butyl (3S)-3-hydroxypyrrolidine-1-carboxylate (2 g, 10.70 mmol), 2,2,2-trifluoroethanol (10.70 g, 106.95 mmol) and triphenylphosphine (3.37 g, 12.83 mmol) in THF (24 mL). The mixture was stirred at 70 C for 16 h. The mixture was concentrated under vacuum and the residue was purified by FCC, eluting with a gradient of EtOAc in heptane. The white solid collected was washed with heptane and the filtrate was concentrated to afford the title compound (1.263 g, 44%), which was used without further purification. Method B HPLC-MS: MH+ requires m/z=270 Found: m/z=214 (M minus tert-butyl), Rt=2.02 min (82%).

Workup

  1. temperaturecooled
  2. concentrationThe mixture was concentrated under vacuum
  3. customthe residue was purified by FCC
  4. washeluting with a gradient of EtOAc in heptane
  5. customThe white solid collected
  6. washwas washed with heptane
  7. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-7be622791b954fdb8389292c0c4c99c7
Source dataset
uspto-grants-2014_11
Patent number
US08895733B2

Reaction notes

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