Tetrahydrofuran → HCID 67234333, compound

HRID 587390Notes

Reaction equation

HRID 587390 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9](=[O:31])[N:10]([C@H:12]2[C@H:16]([C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=3)[CH2:15][N:14]([C:24]([CH:26]3[CH2:30][CH2:29][NH:28][CH2:27]3)=[O:25])[CH2:13]2)[CH3:11])=[CH:4][CH:3]=1.C(O[BH-](O[C:42](=[O:44])[CH3:43])OC(=O)C)(=O)C.[Na+].[CH2:46]1[CH2:50]OC[CH2:47]1>C(OCC)(=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9](=[O:31])[N:10]([C@H:12]2[C@H:16]([C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=3)[CH2:15][N:14]([C:24]([CH:26]3[CH2:30][CH2:29][N:28]([CH:47]4[CH2:43][CH2:42][O:44][CH2:50][CH2:46]4)[CH2:27]3)=[O:25])[CH2:13]2)[CH3:11])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 5049666Sodium triacetoxyborohydrideHCID 58302986HCID 58302986, compound

Product 1

HCID 67234333HCID 67234333, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of [(3S,4R)-4-(4-chloro-phenyl)-1-(pyrrolidine-3-carbonyl)-pyrrolidin-3-yl]-methyl-carbamic acid 4-fluoro-phenyl ester (408 mg, 0.92 mmol) in THF (4 mL) was added under an atmosphere of nitrogen tetrahydro-4H-pyran-4-one (25 mg, 0.25 mmol). After stirring for 15 min. at ambient temperature sodium triacetoxyborohydride (252 mg, 1.19 mmol) was added and stirred continued for 4 h at ambient temperature. The reaction mixture was diluted with ethyl acetate (10 mL) and washed with an aqeuous solution of sodium carbonate (10 mL). The aqueous layer was extracted with ethyl acetate (10 mL) and the combined organic layers were dried of sodium sulfate. Concentration and purification by chromatography (SiO2, ethyl acetate:methanol=100:0 to 80:20) afforded the title compound (115 mg, 24%) as a light yellow oil. MS m/e: 530.3 [M]+.

Workup

  1. additionwas added
  2. washwashed with an aqeuous solution of sodium carbonate (10 mL)
  3. extractionThe aqueous layer was extracted with ethyl acetate (10 mL)
  4. dry with materialthe combined organic layers were dried of sodium sulfate
  5. concentrationConcentration and purification by chromatography (SiO2, ethyl acetate:methanol=100:0 to 80:20)

Sources & evidence

ORD record
ord-a8e6e656e6c74f418355ccec816fbf99
Source dataset
uspto-grants-2016_01
Patent number
US09226916B2

Reaction notes

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