Tetrahydrofuran → HCID 59465667, compound

HRID 1876709Notes

Reaction equation

HRID 1876709 reaction equation
[CH2:1]([N:4]([C:38]1[S:39][CH:40]=[CH:41][N:42]=1)[S:5]([C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH2:18][CH2:17][C@@H:16]([O:19][Si](C(C)(C)C)(C3C=CC=CC=3)C3C=CC=CC=3)[C:15]2=[O:37])=[CH:10][CH:9]=1)(=[O:7])=[O:6])[CH:2]=[CH2:3].C1COCC1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O>[CH2:1]([N:4]([C:38]1[S:39][CH:40]=[CH:41][N:42]=1)[S:5]([C:8]1[CH:9]=[CH:10][C:11]([N:14]2[CH2:18][CH2:17][C@@H:16]([OH:19])[C:15]2=[O:37])=[CH:12][CH:13]=1)(=[O:7])=[O:6])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 2724141Tetrabutylammonium FluorideHCID 53627647(R)-N-allyl-4-(3-(tert-butyldiphenylsilyloxy)-2-oxopyrrolidin-1-yl)-N-(thiazol-2-yl)benzenesulfonamide

Product 1

HCID 59465667HCID 59465667, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirring solution of (R)—N-allyl-4-(3-(tert-butyldiphenylsilyloxy)-2-oxopyrrolidin-1-yl)-N-(thiazol-2-yl)benzenesulfonamide (78.7 g, 127 mmol) and THF (300 mL) under N2, at 0° C., was added tetrabutylammonium fluoride (1.0 M in THF, 255 mL, 255 mmol) dropwise over 20 minutes. The mixture was stirred at ambient temperature for 2 hours. To this solution was added H2O (5 mL) followed by evaporation to dryness. The residue was purified via silica gel using 30% EtOAc in hexanes to obtain the desired alcohol as a white solid (39.5 g, 104 mmol, 82% yield). 1H NMR (400 MHz, DMSO-d6) δ 7.86-7.80 (m, 4H), 7.37 (d, J=4.7 Hz, 1H), 6.93 (d, J=4.7 Hz, 1H), 5.92-5.83 (m, 2H), 5.17 (dd, J=1.3, 10.3 Hz, 1H), 4.98 (q, J=1.4 Hz, 1H), 4.55 (dt, J=5.3, 1.7 Hz, 2H), 4.36-4.30 (m, 1H), 3.81-3.76 (m, 1H), 3.70 (td, J=9.5, 5.4 Hz, 1H), 2.45-2.38 (m, 1H), 1.90-1.80 (m, 1H).

Workup

  1. customfollowed by evaporation to dryness
  2. customThe residue was purified via silica gel using 30% EtOAc in hexanes

Sources & evidence

ORD record
ord-4009005545c24a9f9afaac3b0caa163c
Source dataset
uspto-grants-2012_11
Patent number
US08309587B2

Reaction notes

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